大阪工業大学ロゴ

Original Papers by Prof Araki Masuyama

1.

Studies on Preparation and Properties of
Surface-active Agents

1.1.

Alcohol Ethoxylate Derivatives

1-1-1. "Surface Active Hydroxamic Acids. I. Preparation and Properties of Long-chain Alkyl[oligo(oxyethylene)]oxymethylene-hydroxamic Acids"
Masuyama, A.; Akiyama, K.; Okahara, M. J. Am. Oil Chem. Soc. 1987, 64 (5), 764-768.
1-1-2. "Surface Active Hydroxamic Acids. II. Comparison of Surface Properties of Hydroxamic Acids with Ketones and Methyl Esters with Similar Hydrophilic and Lipophilic Structure"
Masuyama, A.; Akiyama, K.; Okahara, M. J. Am. Oil Chem. Soc. 1987, 64 (7), 1040-1043.
1-1-3. "Preparation and Surface Active Properties of Alcohol Ethoxylates with an Amide Oxime Terminal Group"
Masuyama, A.; Okano, T.; Okahara, M. J. Am. Oil Chem. Soc. 1988, 65 (11), 1830-1833.
1-1-4. "Surface Active Hydroxamic Acids. III. Micellar Catalytic Activity of Water-soluble [α-Alkyloligo(oxyethylene)-ω-yloxy]
acetohydroxamic Acids for Deacylation of p-Nitrophenyl Carboxylates"
Masuyama, A.; Akiyama, K.; Tomita, N.; Okahara, M. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1988, 37 (12), 1108-1113.
1-1-5. "Preparation and Surface Active Properties of Terminal Amide Type of Alcohol Ethoxylates"
Masuyama, A.; Shindoh, A.; Ono, D.; Okahara, M. J. Am. Oil Chem. Soc. 1989, 66 (6), 834-837.
1-1-6. "Preparation and Properties of Surface Active Ketones and Oximes"
Masuyama, A.; Komada, S.; Okahara, M. Tenside Surf. Deterg. 1989, 26 (5), 329-333.
1-1-7. "Application of Surface-Active Amide Oximes to the Collectors for Gallium Ion in an Ion-Flotation System"
Masuyama, M.; Okano, T.; Okahara, M. Ind. Eng. Chem. Res. 1990, 29 (2), 290-294.

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1.2.

Multi-chain Surfactants Bearing Plural Hydrophilic Head Groups (Gemini Surfactants)

1-2-1. "Surface Active Properties of New Types of Amphipathic Compounds with Two Hydrophilic Ionic Groups and Two Lipophilic Alkyl Chains"
Okahara, M.; Masuyama, A.; Sumida, Y.; Zhu, Y.-P. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1988, 37 (9), 746-748.
1-2-2. "Preparation and Surface Active Properties of Amphipathic Compounds with Two Sulfate Groups and Two Lipophilic Alkyl Chains"
Zhu, Y.-P.; Masuyama, A.; Okahara, M. J. Am. Oil Chem. Soc. 1990, 67 (7), 459-463.
1-2-3. "Preparation and Surface-active Properties of New Amphipathic Compounds with Two Phosphate Groups and Two Long-Chain Alkyl Groups"
Zhu, Y.-P.; Masuyama, A.; Okahara, M. J. Am. Oil Chem. Soc. 1991, 68 (4), 268-271.
1-2-4. "Preparation and Properties of Double-chain Surfactants Bearing Two Sulfonate Groups"
Zhu, Y.-P.; Masuyama, A.; Nagata, T.; Okahara, M. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1991, 40 (6), 473-477.
1-2-5. "Preparation and Properties of Double- or Triple-chain Surfactants with Two Sulfonate Groups Derived from N-Acyldiethanolamines"
Zhu, Y.-P.; Masuyama, A.; Kirito, Y.; Okahara, M. J. Am. Oil Chem. Soc. 1991, 68 (7), 539-543.
1-2-6. "Synthesis and Properties of Bis(taurine) Types of Double-chain Surfactants"
Masuyama, A.; Hirono, T.; Zhu, Y.-P.; Okahara, M.; Rosen, M. J. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1992, 41 (4), 301-305.
1-2-7. "Preparation and Properties of Glycerol-Based Double- or Triple-chain Surfactants with Two Hydrophilic Ionic Groups"
Zhu, Y.-P.; Masuyama, A.; Kirito, Y.; Okahara, M.; Rosen, M. J. J. Am. Oil Chem.Soc. 1992, 69 (7), 626-632.
1-2-8. "Synthesis and Properties of Bis(sulfonate) Types of Double-chain Surfactants Bearing a Sulfur Atom in the Connecting Part"
Zhu, Y.-P.; Masuyama, A.; Nakatsuji, Y.; Okahara, M. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1993, 42 (2), 86-94.
1-2-9. "Preparation and Properties of Double-chain Bis(quaternary ammonium) Compounds"
Zhu, Y.-P.; Ishihara, K.; Masuyama, A.; Nakatsuji, Y.; Okahara, M. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1993, 42 (3), 161-167.
1-2-10. "Double-chain Surfactants with Two Carboxylate Groups and Their Relation to Similar Double-chain Compounds"
Zhu, Y.-P.; Masuyama, A.; Kobata, Y.; Nakatsuji, Y.; Okahara, M.; Rosen, M. J. J. Colloid Interface Sci. 1993, 158, 40-45.
1-2-11. "Double-chain Surfactant as a New and Useful Micelle-forming Reagent for Micellar Electrokinetic Chromatography"
Tanaka, M.; Ishida, T.; Araki, T.; Masuyama, A.; Nakatsuji, Y.; Okahara, M.; Terabe, S. J. Chromatogr. 1993, 648, 469-473.
1-2-12. "'Elasticity Index' for the Connecting Groups of Double-chain Amphiphiles Bearing Two Hydrophilic Groups"
Masuyama, A.; Kawano, T.; Zhu, Y.-P.; Kida, T.; Nakatsuji, Y. Chem. Lett. 1993, (12), 2053-2056.
1-2-13. "Unique Interfacial Properties of a Homologous Series of Novel Triple-chain Amphiphiles Bearing Three Anionic Head Groups Derived from 1,1,1-Tris(hydroxymethyl)ethane"
Masuyama, A.; Yokota, M.; Zhu, Y.-P.; Kida, T.; Nakatsuji, Y. J. Chem. Soc., Chem. Commun. 1994, (12), 1435-1436.
1-2-14. "Synergism in Binary Mixtures of Surfactants 12. Mixtures Containing Surfactants with Two Hydrophilic and Two or Three Hydrophobic Groups"
Rosen, M. J.; Gao, T.; Nakatsuji, Y.; Masuyama, A. Colloids and Surfaces A: Physicochem. Eng. Asp. 1994, 88, 1-11.
1-2-15. "Double-chain Surfactants with Two Sulfonate Groups as Micelle-forming Reagents in Micellar Electrokinetic Chromatography of Naphthalene Derivatives"
Harino, H.; Tanaka, M.; Araki, T.; Yasaka, Y.; Masuyama, A.; Nakatsuji, Y.; Ikeda, I.; Funazo, K.; Terabe, S. J. Chromatogr. A 1995, 715, 135-141.
1-2-16. "Solution Properties of Double-Chained Anionic Surfactants with Two Hydrophilic Groups and Two Hydrophobic Groups Having Different Alkyl Chains" (in Japanese)
Kondo, Y.; Yoshino, N.; Isoda, T.; Abe, M.; Masuyama, A.; Nakatsuji, Y. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1995, 44 (12), 1050-1054.
1-2-17. "Pressure-Area Isotherms for Double-Chain Amphiphiles Bearing Two Hydroxyl Groups Derived from Diepoxides"
Sumida, Y.; Masuyama, A.; Oki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I.; Nojima, M. Langmuir 1996, 12 (16), 3986-3990.
1-2-18. "Separation of Pollutant Phenols by Micellar Electrokinetic Chromatography with Double-Chain Surfactants Having Two Sulfonate Groups"
Harino, H.; Tsunoi, S.; Yoshioka, J.; Araki, T.; Masuyama, A.; Nakatsuji, Y.; Ikeda, I.; Tanaka, M. Anal. Sci. 1998, 14 (8), 719-724.
1-2-19. "Ozone-Cleavable Gemini Surfactants, A New Candidate for an Environmentally Friendly Surfactant"
Masuyama, A.; Endo, C.; Takeda, S.; Nojima, M. Chem. Commun. 1998, (18), 2023-2024.
1-2-20. "Stable Vesicles Made from New Triple-Chain Amphiphiles: Long-Term Stability toward Leakage of the Trapped Substances"
Sumida, Y.; Masuyama, A.; Maekawa, H.; Takasu, M.; Kida, T.; Nakatsuji, Y.; Ikeda, I.; Nojima, M. Chem. Commun. 1998, (21), 2385-2386.
1-2-21. "π-A Isotherms for Triple-Chain Amphiphiles Bearing Two or Three Hydroxyl Groups. Effect of the Backbone Structure on the Adsorption Behavior of the Molecules on the Surface"
Sumida, Y.; Oki, T.; Masuyama, A.; Maekawa, H.; Nishiura, M.; Kida, T.; Nakatsuji, Y.; Ikeda, I.; Nojima, M. Langmuir 1998, 14 (26), 7450-7455.
1-2-22. "Ozone-Cleavable Gemini Surfactants. Their Surface-Active Properties, Ozonolysis, and Biodegradability"
Masuyama, A.; Endo, C.; Takeda, S.; Nojima, M.; Ono, D.; Takeda, T. Langmuir 2000, 16 (2), 368-373.
1-2-23. "Behavior of Self-Organized Molecular Assemblies Composed of Phosphatidylcholines and Synthetic Triple-Chain Amphiphiles in Water"
Sumida, Y.; Masuyama, A.; Takasu, M.; Kida, T.; Nakatsuji, Y.; Ikeda, I.; Nojima, M. Langmuir 2000, 16 (21), 8005-8009.
1-2-24. "New pH-Sensitive Vesicles. Release Control of Trapped Materials from the Inner Aqueous Phase of Vesicles Made from Triple-Chain Amphiphiles Bearing Two Carboxylate Groups"
Sumida, Y.; Masuyama, A.; Takasu, M.; Kida, T.; Nakatsuji, Y.; Ikeda, I.; Nojima, M. Langmuir 2001, 17 (3), 609-612.

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1.3.

Chemocleavable Surfactants

1-3-1. "Preparation of New Acetal Type Cleavable Surfactants from Epichlorohydrin"
Ono, D.; Masuyama, A.; Okahara, M. J. Org. Chem. 1990, 55 (14), 4461-4464.
1-3-2. "Cleavable Surfactants of the Acetal Type. Properties of New Acetal Types of Cleavable Surfactants Derived from Epichlorohydrin"
Ono, D.; Masuyama, A.; Tanaka, T.; Okahara, M. Tenside Surf. Deterg. 1992, 29 (6), 412-417.
1-3-3. "Preparation and Properties of Bis(sodium carboxylate) Types of Cleavable Surfactants Derived from Diethyl Tartrate and Fatty Carbonyl Compounds"
Ono, D.; Tanaka, T.; Masuyama, A.; Nakatsuji, Y.; Okahara, M. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1993, 42 (1), 10-16.
1-3-4. "Preparation, Surface-active Properties and Acid Decomposition Profiles of New 'Soap' Bearing a 1,3-Dioxolane Ring"
Ono, D.; Masuyama, A.; Nakatsuji, Y.; Okahara, M.; Yamamura, S.; Takeda, T. J. Am. Oil Chem. Soc. 1993, 70 (1), 29-36.
1-3-5. "Synthesis and Properties of Soap Types of Cleavable Surfactants Bearing a 1,3-Dioxolane Ring Derived from
Long-chain Epoxides and Ethyl Levulinate"
Ono, D.; Yamamura, S.; Nakamura, M.; Takeda, T.; Tanaka, T.; Masuyama, A.; Nakatsuji, Y. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1993, 42 (12), 965-971.
1-3-6. "Unique Betaine Types of Surfactants Bearing a 1,3-Dioxolane Ring"
Masuyama, A.; Ono, D.; Yamamoto, A.; Kida, T.; Nakatsuji, Y.; Takeda, T. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1995, 44 (6), 446-450.
1-3-7. "Biodegradation of Different Carboxylate Types of Cleavable Surfactants Bearing a 1,3-Dioxolane Ring"
Ono, D.; Yamamura, S.; Nakamura, M.; Takeda, T.; Masuyama, A.; Nakatsuji, Y. J. Am. Oil Chem. Soc. 1995, 72 (7), 853-856.
1-3-8. "Emulsion Polymerization by Using Chemocleavable Emulsifiers Derived from 1-O-Alkylglycerols"
Ono, D.; Takahashi, Y.; Sato, H.; Shizuma, M.; Masuyama, A.; Nakamura, M. J. Oleo Sci. 2011, 60 (3), 145-151.

1.4.

Surfactants Derived from Sucrose

1-4-1. "Preparation of Trihydroxycarboxylates Bearing a Long-chain. Alkyl Acetal Group from Glucono-1,5-lactone"
Kida, T.; Masuyama, A.; Okahara, M. Tetrahedron Lett. 1990, 31 (41), 5939-5942.
1-4-2. "New Cleavable Surfactants Derived from Glucono-1,5-lactone"
Kida, T.; Morishima, N.; Masuyama, A.; Nakatsuji, Y. J. Am. Oil Chem. Soc. 1994, 71 (7), 705-710.
1-4-3. "A Facile Synthesis of Lipophilic Acetal Derivatives of L-Ascorbic Acid (Vitamin C)"
Kida, T.; Masuyama, A.; Nakatsuji, Y. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1994, 43 (12), 1086-1088.
1-4-4. "Preparation and Properties of New Surfactants Containing D-Glucosamine as the Building Block"
Kida, T.; Yurugi, K.; Masuyama, A.; Nakatsuji, Y.; Ono, D.; Takeda, T. J. Am. Oil Chem. Soc. 1995, 72 (7), 773-780.
1-4-5. "Selective Transport of Saccharides through a Bulk Liquid Membrane Using Reversed Micelle Carriers"
Kida, T.; Furue, D.; Masuyama, A.; Nakatsuji, Y.; Ikeda, I. Chem. Lett. 1996, (9), 733-734.
1-4-6. "Preparation and Properties of Nonionic Surfactants with One Alkyl Chain and Two Sugar-Amide Head Groups"
Kida, T.; Isogawa, K.; Morishima, N.; Zhang, W.; Masuyama, A.; Nakatsuji, Y.; Ikeda, I. J. Jpn. Oil Chem. Soc. 1998, 47 (1), 41-49.

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1.5.

Other Types of Surfactants

1-5-1. "Synthesis and Properties of Surfactants Derived from Highly Branched Tertiary Carboxylic Acids" (in Japanese)
Nakatsuji, Y.; Ueno, S.; Kidera, Y.; Masuyama, A.; Okahara, M.; Kawasaki, H. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1992, 41 (10), 1061-1066.

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2.

Studies on Preparation and Properties of Crown Ethers and Related Compounds

2-1. "Complexing Ability of N-Oligoethylene Glycol Monoaza Crown Ethers with Sodium and Potassium Cations"
Masuyama, A.; Nakatsuji, Y.; Ikeda, I.; Okahara, M. Tetrahedron Lett. 1981, 22 (46), 4665-4668.
2-2. "Complexing Abilities of N-[ω-(Long-chain alkyl)oligo(oxyethylene)] Monoaza Crown Ethers with Metal Cations in Water and in Methanol"
(in Japanese) Masuyama, A.; Kuo, P.-L.; Ikeda, I.; Okahara, M. Nippon Kagaku Kaishi 1983, (2), 249-254.
2-3. "Preparation of Urethane-type Crown Ethers by Thermolytic Reaction of Aminimides"
Masuyama, A.; Nakamura, Y.; Iwasaki, T.; Okahara, M. Synth. Commun. 1985, 15 (6), 521-526.
2-4. "Efficient Solvent for Supported Liquid Membrane Transport with Lipophilic Monoaza-18-crown-6"
Nakatsuji, Y.; Shimizu, H.; Morita, H.; Masuyama, A.; Okahara, M. Chem. Lett. 1992, (11), 2185-2188.
2-5. "Complexation Property of a Novel Macrobicyclic Polyether with Two Amide Moieties toward Alkali Metal and Alkaline Earth Metal Cations"
Nakatsuji, Y.; Inoue, T.; Masuyama, A.; Okahara, M. Bull. Chem. Soc. Jpn. 1992, 65 (12), 3490-3492.
2-6. "Complexation of Acyclic Ligands Having Two Terminal Quinoline Units with Alkali Metal Cations"
Sugimoto, M.; Fujiwara, K.; Wakita, R.; Kida, T.; Masuyama, A.; Nakatsuji, Y.; Okahara, M. Supramol. Chem. 1993, 2, 145-151.
2-7. "A pH-dependent Exchange of Na+ and Ca2+ in a Liquid Membrane System"
Nakatsuji, Y.; Morita, H.; Masuyama, A.; Kida, T. Chem. Lett. 1993, (10), 1743-1746.
2-8. "Synthetic Noncyclic Ionophores with Multiple Carboxylate Groups for Alkaline Earth Metal Cations"
Nakatsuji, M.; Matsumoto, M.; Masuyama, A.; Kida, T. J. Incl. Phenom. 1994, 18 (4), 377-383.
2-9. "New Type of C-Pivot Tripode Ligands for Complexation towards Alkali Metal Cations"
Nakatsuji, Y.; Kita, K.; Masuyama, A.; Kida, T. Chem. Lett. 1995, (1), 51-52.
2-10. "Synthesis, Structure, and Complexation Properties of Monoazacryptands"
Nakatsuji, Y.; Sunagawa, T.; Masuyama, A.; Kida, T.; Ikeda, I. Chem. Lett. 1995 (6), 445-446.
2-11. "Effects of Connecting Moieties in Crown Polymers on Complexation with Alkali Metal Cations"
Nakatsuji, Y.; Tsubakihara, M.; Masuyama, A.; Kida, T.; Okahara, M.; Ikeda, I. J. Jpn. Oil Chem. Soc. (YUKAGAKU) 1995, 44 (7), 509-511.
2-12. "Selective Transport of Lithium Ion Using Noncyclic Proton-ionizable Ionophores through Bulk and Emulsion Liquid Membranes"
Nakatsuji, Y.; Inoue, M.; Matsumoto, M.; Masuyama, A.; Kida, T. J. Membrane Sci. 1995, 104, 165-172.
2-13. "Alkali Metal Cation Recognition at an Air-Water Interface by Lipophilic Double-Armed Crown Ethers"
Nakatsuji, M.; Muraoka, M.; Matsuoka, H.; Kida, T.; Masuyama, A.; Ikeda, I. J. Jpn. Oil Chem. Soc. 1997, 46 (8), 931-934.
2-14. "Double Uphill Transport of Ca2+-Na+ or Ca2+-K+ in Opposite Directions by Lipophilic Crown Ethers with Two Carboxylic Acid Moieties"
Nakatsuji, Y.; Muraoka, M.; Wada, M.; Morita, H.; Masuyama, A.; Kida, T.; Ikeda, I. J. Org. Chem. 1997, 62 (18), 6231-6235.

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3.

Studies on Ozonolysis of Various Organic Compounds and Preparation of Organic Peroxides

3-1. "Synthesis of 1,2,4-Dioxazolidine Derivatives by the Ozonolysis of Indenes in the Presence of Primary Amines"
Ushigoe, Y.; Satake, S.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Chem. Soc., Perkin Trans. 1 1997, (13), 1939-1942.
3-2. "Synthesis of Hydroxy(or Hydroperoxy)-Substituted 1,2,4-Trioxacycloalkanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals"
Ushigoe, Y.; Torao, Y.; Masuyama, A.; Nojima, M. J. Org. Chem. 1997, 62 (15), 4949-4954.
3-3. "New Methods for the Synthesis of Oxy-Functionalized
1,2,4-Trioxanes and 1,2,4-Trioxepanes from Unsaturated Hydroperoxy Acetals"
Ushigoe, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J. Tetrahedron Lett. 1997, 38 (50), 8753-8756.
3-4. "Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation"
Kawamura, S.; Takeuchi, R.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Org. Chem. 1998, 63 (16), 5617-5622.
3-5. "Synthesis of Novel Hydroperoxy-Substituted 1,2,4,5-Tetroxepanes and 1,2,4,5-Tetroxocanes"
Nonami, Y.; Ushigoe, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J. Tetrahedron Lett. 1998, 39 (36), 6597-6600.
3-6. "Chemical Transformation of Solvent-derived Ozonolysis Products: Improved Synthesis of Polycyclic 1,2,4,6-Tetroxepanes from α-Alkoxy α'-Hydroperoxy Cyclic Ethers and Aldehydes"
McCullough, K. J.; Ushigoe, Y.; Tanaka, S.; Masuyama, A.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1998, (18), 3053-3057.
3-7. "Chemical Transformation of Solvent-derived Ozonolysis Products: Acid-catalysed Reactions of α-Alkoxy α'-Hydroperoxy Isochromans with Aldehydes"
McCullough, K. J.; Ushigoe, Y.; Tanaka, S.; Kawamura, S.; Masuyama, A.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1998, (18), 3059-3064.
3-8. "Ozonolyses of 3-Benzoyloxy- and 3-Trimethylsiloxy-Substituted 2-Phenylindenes in Methanol: Substituent-Dependent
Modes of Capture of the Carbonyl Oxide Intermediates by the Solvent"
McCullough, K. J.; Takeuchi, R.; Masuyama, A.; Nojima, M. J. Org. Chem. 1999, 64 (6), 2137-2139.
3-9. "Synthesis, Crystal Structure and Anti-Malarial Activity of Novel Spiro-1,2,4,5-Tetraoxacycloalkanes"
Tsuchiya, K.; Hamada, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J.; Kim, H.-S.; Shibata, Y.; Wataya, Y. Tetrahedron Lett. 1999, 40 (21), 4077-4080.
3-10. "Synthesis and Antimalarial Activity of Cyclic Peroxides, 1,2,4,5,7-Pentoxocanes, and 1,2,4,5-Tetroxanes"
Kim, H.-S.; Shibata, Y.; Wataya, Y.; Tsuchiya, K.; Masuyama, A.; Nojima, M. J. Med. Chem. 1999, 42 (14), 2604-2609.
3-11. "Synthetic Methods for Unsymmetrically-Substituted 1,2,4,5-Tetroxanes and of 1,2,4,5,7-Pentoxocanes"
Kim, H.-S.; Tsuchiya, K.; Shibata, Y.; Wataya, Y.; Ushigoe, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Chem. Soc., Perkin Trans. 1 1999, (13), 1867-1870.
3-12. "Synthesis, Crystal Structure and Antimalarial Activity of Novel 1,2,5,6-Tetraoxacycloalkanes from 2,3-Dihydroperoxy-2-phenylnorbonane"
McCullough, K. J.; Nonami, Y.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Wataya, Y. Tetrahedron Lett. 1999, 40 (51), 9151-9154.
3-13. "Haolnium Ion-Mediated Reaction of Unsaturated Hydroperoxy Acetals. Competition between the Formation of Cyclic Peroxides and the Migration of the Methoxy (or Hydroxy) Group"
Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Org. Chem. 2000, 65 (4), 1069-1075.
3-14. "Synthesis and Anti-Malarial Activity of Yingzhaosu A Analogues from Unsaturated Hydroperoxy Acetals"
Tokuyasu, T.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Wataya, Y. Tetrahedron Lett. 2000, 41 (17), 3145-3148.
3-15. "Substituted 1,2-Dioxanes and 1,2-Dioxepanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals"
Tokuyasu, T.; Ito, T.; Masuyama, A.; Nojima, M. Heterocycles 2000, 53 (6), 1293-1304.
3-16. "Synthesis, Crystal Structure and Antimalarial Activity of Functionalized Spiro-1,2,4,5-tetraoxacycloalkanes from Unsaturated Hydroperoxy Peracetals"
Nonami, Y.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCuH.-S.; Wataya, Y. Tetrahedron Lett. 2000, 41 (23), 4681-4684.
3-17. "Yingzhaosu A Analogues: Synthesis by the Ozonolysis of Unsaturated Hydroperoxides, Structural Analysis and Determination of Anti-malarial Activity"
Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J.; Kim, H.-S.; Wataya, Y. Tetrahedron 2001, 57 (28), 5979-5989.
3-18. "The Synthesis and Crystal Structure Analysis of Novel Macrocyclic Peroxides"
McCullough, K. J.; Ito, T.; Tokuyasu, T.; Masuyama, A.; Nojima, M. Tetrahedron Lett. 2001, 42 (32), 5529-5532.
3-19. "Synthesis and Antimalarial Activity of Novel Medium-Sized 1,2,4,5-Tetraoxacycloalkanes"
Kim, H.-S.; Nagai, Y.; Ono, K.; Begum, K.; Wataya, Y.; Hamada, Y.; Tsuchiya, K.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Med. Chem. 2001, 44 (14), 2357-2361.
3-20. "Ozonolyses of Cyclopent-1-enylbenzenes in Micellar Aqueous Solutions"
Masuyama, A.; Yamakawa, S.; Nojima, M. Langmuir 2001, 17 (24), 7507-7512.
3-21. "Ozonolysis of 1-Alkyl-substituted 1-tert-Butylethylenes and Highly Methylated Methylenecycloalkanes. The Influence of the Substituent Steric Bulk on the Direction of Cleavage of the Primary Ozonides"
Kawamura, S.; Yamakoshi, H.; Abe, M.; Masuyama, A.; Nojima, M. Tetrahedron 2002, 58 (5), 891-896.
3-22. "Synthesis and Notable Antimalarial Activity of Acyclic Peroxides, 1-(Alkyldioxy)-1-(methyldioxy)cyclododecanes"
Hamada, Y.; Tokuhara, H.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Ono, K.; Ogura, N.; Wataya, Y. J. Med. Chem. 2002, 45 (6), 1374-1378 (2002).
3-23. "Multifunctional Anti-angiogenic Activity of the Cyclic Peroxide ANO-2 with Antitumor Activity"
Arakawa, K.; Endo, Y.; Kimura, M.; Yoshida, T.; Kitaoka, T.; Inakazu, T.; Nonami, Y.; Abe, M.; Masuyama, A.; Nojima, M.; Sasaki, T. Int. J. Cancer 2002, 100 (2), 220-227.
3-24.
 
"Co(III)-Alkyl Complex- and Co(III)-Alkylperoxo Complex-Catalyzed Triethylsilylperoxidation of Alkenes with Molecular Oxygen and Triethylsilane"
Tokuyasu, T.; Kunikawa, S.; Masuyama, A.; Nojima, M. Org. Lett. 2002, 4 (21), 3595-3598.
3-25. "Antimalarial Activity of Yingzhaosu A Analogues"
Kim, H.-S.; Begum, K.; Ogura, N.; Wataya, Y.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Med. Chem. 2002, 45 (21), 4732-4736.
3-26. "Synthesis of Novel Macrocyclic Peroxides by Bis(sym-collidine)iodine (I) hexafluorophosphate-Mediated Cyclization of Unsaturated Hydroperoxides and Unsaturated Alcohols"
Ito, T.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. Tetrahedron 2003, 59 (4), 525-536.
3-27. "New Approaches to the Synthesis of Spiro-peroxylactones"
McCullough, K. J.; Tokuhara, H.; Masuyama, A.; Nojima, M. Org. Biomol. Chem. 2003, 1 (9), 1522-1527.
3-28. "Antimalarial Activity of Novel 1,2,5,6-Tetraoxacycloalkanes and 1,2,5-Trioxacycloalkanes"
Kim, H.-S.; Begum, K.; Ogura, N.; Wataya, Y.; Nonami, Y.; Ito, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Med. Chem. 2003, 46 (10), 1957-1961.
3-29. "Synthesis of Antimalarial Yingzhaosu A Analogues by the Peroxidation of Dienes with Co(II)/O2/Et3SiH"
Tokuyasu, T.; Kunikawa, S.; Abe, M.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Begum, K.; Wataya, Y. J. Org. Chem. 2003, 68 (19), 7361-7367.
3-30. "Synthesis of Cyclic Peroxides by Chemo- and Regioselective Peroxidation of Dienes with Co(II)/O2/Et3SiH"
Tokuyasu, T.; Kunikawa, S.; McCullough, K. J.; Masuyama, A.; Nojima, M. J. Org. Chem. 2005, 70 (1), 251-260.
3-31. "Co-Catalyzed Autoxidation of Alkene in the Presence of Silane. The Effect of the Structure of Silanes on the Efficiency of the Reaction and on the Product Distribution"
Wu, J.-M.; Kunikawa, S.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Wataya, Y. Tetrahedron 2005, 61 (42), 9961-9968.
3-32. "Proteome Analysis of New Antimalarial Endoperoxide against Plasmodium falciparum"
Aly, N. S. M.; Hiramoto, A.; Sanai, H.; Hiraoka, O.; Hiramoto, K.; Kataoka, H.; Wu, J.-M.; Masuyama, A.; Nojima, M.; Kawai, S.; Kim, H.-S.; Wataya, Y. Parasitol. Res. 2007, 100, 1119-1124.
3-33. "Antimalarial Activity of Endoperoxide Compound 6-(1,2,6,7-Tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol"
Sato, A.; Hiramoto, A.; Morita, M.; Matsumoto, M.; Komichi, Y.; Nakase, Y.; Tanigawa, N.; Hiraoka, O.; Hiramoto, K.; Hayatsu, H.; Higaki, K.; Kawai, A.; Masuyama, A.; Nojima, M.; Wataya, Y.; Kim, H.-S. Parasitol. Int. 2011, 60 (3), 270-273.
3-34. "Antimalarial Activity of 6-(1,2,6,7-Tetraoxaspiro[7.11]nonadec-1-ol (N-251) and Its Carboxylic Acid Derivatives"
Sato, A.; Kawai, S.; Hiramoto, A.; Morita, M.; Tanigawa, N.; Nakase, Y.; Komichi, Y.; Matsumoto, M.; Hiraoka, O.; Hiramoto, K.; Tokuhara, H.; Masuyama, A.; Nojima, M.; Higaki, K.; Hayatsu, H.; Wataya, Y.; Kim, H.-S. Parasitol. Int. 2011, 60 (4), 488-492.
3-35. "Plasmodium falciparum Endoplasmic Reticulum-Resident Calcium Binding Protein Is a Possible Target of Synthetic Antimalarial Endoperoxides, N-89 and N-251"
Morita, M.; Sanai, H.; Hiramoto, A.; Sato, A.; Hiraoka, O.; Sakura, T.; Kaneko, O.; Masuyama, A.; Nojima, M.; Wataya, Y.; Kim, H.-S. J. Proteome Res. 2012, 11 (12), 5704-5711.
3-36. "Stage Specific Activity of Synthetic Antimalarial Endoperoxides, N-89 and N-251, against Plasmodium falciparum"
Morita, M.; Koyama, T.; Sanai, H.; Sato, A.; Hiramoto, A.; Masuyama, A.; Nojima, M.; Wataya, Y.; Kim, H.-S. Parasitol. Int. 2015, 64 (1), 113-117.

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4.

Studies on Radical Reactions of Hydroperoxides

4-1. "Iron(II)-mediated Fragmentation of Unsaturated Hydroperoxy Acetals: A Rapid Synthetic Route to 13-Membered Macrolides"
McCullough, K. J.; Motomura, Y.; Masuyama, A.; Nojima, M. Chem. Commun. 1998, (11), 1173-1174.
4-2. "Reaction of Highly Methylated 2-Methylenecycloalkyl Hydroperoxides with FeSO4/CuCl2. Remarkably Efficient 5-endo-trig or 6-endo-trig Cyclization of the Intermediate Carbon Radicals"
Nonami, Y.; Baran, J.; Sosnicki, J.; Mayr, H.; Masuyama, A.; Nojima, M. J. Org. Chem. 1999, 64 (11), 4060-4063.
4-3. "Regioselective Radical Cyclization Initiated by the Reaction of Allylic Hydroperoxides with Iron(II) Sulfate"
Masuyama, M.; Sugawara, T.; Nojima, M.; McCullough, K. J. Tetrahedron 2003, 59 (3), 353-366.

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5.

Studies on Oxidation Reactions in Water

5-1. "Amphiphilic α-Alkoxyalkyl Hydroperoxide (α-AHP): A New Oxidising Reagent in Aqueous Media"
Masuyama, A.; Fukuoka, K.; Wakita, M.; Nojima, M. Chem. Commun. 2000, (18), 1727-1728.
5-2. "New Protocol for Oxidation in Water: Micellar Oxidation Systems Composed of Novel Amphiphilic Hydroperoxides"
Masuyama, A.; Fukuoka, K.; Katsuyama, N.; Nojima, M. Langmuir 2004, 20 (1), 82-89.
5-3. "Alternative Protocol for Oxidation in Water: An Effective Epoxidation System Promoted by the Combination of Oxone® and an Amphiphilic Ketone"
Masuyama, A.; Yamaguchi, T.; Abe, M.; Nojima, M. Tetrahedron Lett. 2005, 46 (2), 213-216.

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6.

Other Studies

6-1. "Preparation and Thermolysis of N-Ammonioamidates Containing Hydroxyl Group in Acyl Moiety"
Masuyama, A.; Tsuchiya, K.; Okahara, M. Bull. Chem. Soc. Jpn. 1985, 58 (10), 2855-2859.
6-2. "Preparation and Thermolysis of N-Ammonioamidates as Model Precursors of New Type of Segmented Poly(ether-urethane)s"
Masuyama, A.; Iwasaki, T.; Okahara, M. Makromol. Chem. 1986, 187 (8), 1833-1841.
6-3. "2-Chloro-1-(chloromethyl)ethyl Methoxymethyl Ether as a Reagent for Acetonylation of Alcohols and Phenol"
Gu, X.-P.; Ikeda, I.; Komada, S.; Masuyama, A.; Okahara, M. J. Org. Chem. 1987, 51 (26), 5425-5427.
6-4. "A Facile Synthesis of Polyglycidyl Ethers from Polyols and Epichlorohydrin"
Kida, T.; Yokota, M.; Masuyama, A.; Nakatsuji, Y.; Okahara, M. Synthesis 1993, (5), 487-489.
6-5. "Syntheses, Structure Analyses, and Reactions of 1,3,5-Trioxepanes and Related Compounds"
McCullough, K. J.; Masuyama, A.; Morgan, K. M.; Nojima, M.; Okada, Y.; Satake, S.; Takeda, S. J. Chem. Soc., Perkin Trans. 1 1998, (15), 2353-2362.
6-6. "Novel Substituent Effects on the Mechanism of the Thermal Denitrogenation of 2,3-Diazabicyclo[2.2.1]hept-2-ene Derivatives, Stepwise versus Concerted"
Abe, M.; Ishihara, C.; Kawanami, S.; Masuyama, A. J. Am. Chem. Soc. 2005, 127 (1), 10-11.
6-7. "Nucleophilic Addition to 3,4-cis-Diacetyl-1,2,3,4-tetramethyl-cyclo-1-butene: Remarkably Fast Intramolecular Hemiketalization"
Baran, J.; Sosnicki, J. G.; Nonami, Y.; Masuyama, A.; Nojima, M. Tetrahedron Lett. 2005, 46 (5), 747-750.
6-8. "Notable Temperature Effect on the Stereoselectivity in the Photochemical [2+2] Cycloaddition Reaction (Paternò-Büchi Reaction) of 2,3-Dihydrofuran-3-ol Derivatives with Benzophenone"
Abe, M.; Terazawa, M.; Nozaki, K.; Masuyama, A.; Hayashi, T. Tetrahedron Lett. 2006, 47 (15), 2527-2530.
6-9. "Experimental Probe for Hyperconjugative Resonance Contribution in Stabilizing the Singlet State of 2,2-Dialkoxyl-1,3-diyls: Regioselective 1,2-Oxygen Migration"
Abe, M.; Hattori, M.; Takegami, A.; Masuyama, A.; Hayashi, T.; Seki, S.; Tagawa, S. J. Am. Chem. Soc. 2006, 128 (24), 8008-8014.
6-10. "A Matrix Isolation Study of 2-Isopropylidenecyclopentane-1,3-diyl (Berson-Type Diradical)"
Abe, M.; Kawanami, S.; Masuyama, A.; Hayashi, T. J. Org. Chem. 2006, 71 (17), 6607-6610.
6-11. "Preparation and Condensation Reactions of a New Light-fluorous Mukaiyama Reagent: Reliable Purification with Fluorous Solid Phase Extraction for Esters and Amides"
Matsugi, M.; Hasegawa, M.; Sadachika, D.; Okamoto, S.; Tomioka, M.; Ikeya, Y.; Masuyama, A.; Mori, Y. Tetrahedron Lett. 2007, 48 (23), 4147-4150.
6-12. "Surface Modification of Organic-Inorganic Hybrid Insulator for Printable Organic Field-effect Transistors"
Watanabe, M.; Muro, K.; Hamada, T.; Tamai, T.; Masuyama, A.; Naito, H.; Matsukawa, K. Chem. Lett. 2009, 38 (1), 34-35.
6-13. "Polymer Particles Incorporating ZrO2 Nanoparticles Prepared by Miniemulsion Polymerization"
Tamai, T.; Watanabe, M.; Minami, Y.; Okazaki, S.; Masuyama, A.; Matsukawa, K. Chem. Lett. 2011, 40 (1), 37-39.
6-14. "Stereocontrolled Synthesis of Substituted Bicyclic Ethers through Oxy-Favorskii Rearrangement: Total Synthesis of (±)-Communiol E"
Kobayashi, S.; Kinoshita, T.; Kawamoto, T.; Wada, M.; Kuroda, H., Masuyama, A.; Ryu, I. J. Org. Chem. 2011, 76 (17), 7096-7103.
6-15. "Rapid Access to 6-Bromo-5,7-dihydroxyphthalide 5-Methyl Ether by a CuBr2-mediated Multi-step Reaction: Concise Total Syntheses of Hericenone J and 5'-Deoxohericenone C (hericene A)"
Kobayashi, S.; Ando, A.; Kuroda, H.; Ejima, S.; Masuyama, A.; Ryu, I. Tetrahedron 2011, 67 (47), 9087-9092.
6-16. "Optimization of Lactobionic Acid Production by Acetobacter orientalis Isolated from Caucasian Fermented Milk, 'Caspian Sea Yogurt'"
Kiryu, T.; Yamauchi, K.; Masuyama, A.; Ooe, K.; Kimura, T.; Kiso, T.; Nakano, H.; Murakami, H. Biosci. Biotechnol. Biochem. 2012, 76 (2), 361-363.
6-17. "Total Synthesis and Structural Revision of Hericerin"
Kobayashi, S.; Inoue, T.; Ando, A.; Tamanoi, H.; Ryu, I.; Masuyama, A. J. Org. Chem. 2012, 77 (13), 5819-5822.
6-18. "Hybrid Films Prepared from Latex Particles Incorporating Metal Oxide Nanoparticles"
Tamai, T.; Okazaki, S.; Watanabe, M.; Minami, Y.; Masuyama, A.; Matsukawa, K. Res. Chem. Intermed. 2013, 39 (1), 291-300.
6-19. "Evaluation of Cyclopentyl Methyl Ether (CPME) as a Solvent for Radical Reactions"
Kobayashi, S.; Kuroda, H.; Ohtsuka, Y.; Kashihara, T.; Masuyama, A.; Watanabe, K. Tetrahedron 2013, 69 (10), 2251-2259.
6-20. "Divergent Synthesis of Bioactive Resorcinols Isolated from the Fruiting Bodies of Hericium erinaceum: Total Syntheses of Hericenones A, B, and I, Hericenols B-D, and Erinacerins A and B"
Kobayashi, S.; Tamanoi, H.; Hasegawa, Y.; Segawa, Y.; Masuyama, A. J. Org. Chem. 2014, 79 (11), 5277-5238.
6-21. "Selective Preparation of Monobenzyl Glyceryl Ethers by the Condensation Reaction of Glycerol with Benzyl Alcohols in the Presence of Zeolite Catalysts"
Kubota, M.; Sakamoto, A.; Komatsu M.; Maeno, K.; Masuyama, A. J. Oleo Sci. 2014, 63 (10), 1057-1062.
6-22. "Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction"
Kobayashi, S.; Yokoi, T.; Inoue, T.; Hori, Y.; Saka, T.; Shimomura, T.; Masuyama, A. J. Org. Chem. 2016, 81 (4), 1484-1498.
6-23. "Grignard Reactions in Cyclopentyl Methyl Ether"
Kobayashi, S.; Shibukawa, K.; Miyaguchi, Y.; Masuyama, A. Asian J. Org. Chem. 2016, 5 (5), 636-645.
6-24. "Syntheses of (-)-Tripterifordin and (-)-Neotripterifordin from Stevioside"
Kobayashi, S.; Shibukawa, K.; Hamada, Y.; Kuruma, T.; Kawabata, A.; Masuyama, A. J. Org. Chem. 2018, 83 (3), 1606-1613.
6-25. "Total Syntheses and Endoplasmic Reticulum Stress Suppressive Activities of Hericenes A-C and Their Derivatives"
Kobayashi, S; Hamada, Y.; Yasumoto, T.; Hashino, Y.; Masuyama, A.; Nagai, K. Tetrahedron Lett. 2018, 59 (18), 1733-1736.
   

 

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