兵庫県立大学理学研究科物質科学専攻

物質反応論Ⅱ研究室

Organic Chemistry Laboratory

研究業績

Achievemnets

1980-1999 | 2000-2009 | 2010-2019 | 2020-2021

1999

Diastereo-Differentiation during 2,4-Pentanediol Tethered Simmons-Smith Type Cyclopropanation: Reaction Species of Hydroxyl Group Directed Zinc Carbenoid Addition. Sugimura, T., Yoshikawa, M., Mizuguchi, M. & Tai, A. Chem. Lett., 831-832 (1999).
Regiocontrol of Diels-Alder Reaction of Conjugate 1-Trienol Ether in Chiral Tropilidene with TCNE. Sugimura, T., Nagano, S., Kohno, H., Fujita, M. & Tai, A. Chem. Lett., 179-180 (1999).
Rapid [1,5] Hydrogen Migration on 7-Alkoxycarbonyltropilidenes under Conformational Regulation. Sugimura, T., Kohno, H., Nagano, S., Nishida, F. & Tai, A. Chem. Lett., 1143-1144 (1999).
Recent Progress in Tartaric Acid-Modified Raney Nickel System for Enantio-differentiating Hydrogenation. Sugimura, T. Catal. Surv. Jpn. 3, 37-42 (1999).
Enantio-differentiating Hydrogenation of Methyl 2-Furoylacetate and Its Analogs over Tartaric Acid-Modified Raney Nickel. Nakagawa, S. et al. Chem. Lett., 1055-1056 (1999).
Effective Trap of Zwitterionic Intermediate during Oxigenation of Elactron-Rich Naphthalenes with Singlet Oxygen by the Intramolecular Alcohol. Fujita, M., Ohshiba, M., Yamasaki, Y., Sugimura, T. & Tai, A. Chem. Lett., 139-140 (1999).

1998

Diastereo-differentiating Coupling of Phenoxy Radical Moiety Controlled by 2,4-Pentanediol Tether. Preparation of Optically Active Pummerer,s Ketone Analogs. Yamaguchi, K., Sugimura, T., Nishida, F. & Tai, A. Tetrahedron Lett. 39, 4521-4524 (1998).
Field and Electroantennogram Responses of the Pine Sawfly, Diprion Nipponica, to the Chemical Synthetic Pheromone Candidates. Tai, A. et al. Biosci. Biotech. Biochem. 62, 607-608 (1998).
Efficient Diastereodifferentiating E–Z Photoisomerization of Cyclooctene Tethered to Intramolecular Sensitizer through Optically Active Pentane-2,4-diyl Unit. Sugimura, T. et al. Chem. Lett., 323-324 (1998).
The First Asymmetric Synthesis of Optically Active Tropilidenes. Highly Regio- and Diastereo-differentiating Addition of Diazo Ester to Aromatic Ring Using 2,4-Pentanediol as Chiral Linking Bridge. Sugimura, T., Nagano, S. & Tai, A. Chem. Lett., 45-46 (1998).
Selective Preparation of Optically Pure (R,R)-1,1':5',1"-Ternaphthalene-2,2',6',2"-tetraol: A New Higher Homolog of BINOL. Sugimura, T., Inoue, S. & Tai, A. Tetrahedron Lett. 39, 6487-6490 (1998).
Diastereoface-differentiating oxidation of 1-cyclohexenyl ether using a 2,4-pentanediol tether. Sugimura, T. et al. Tetrahedron: Asymmetry 9, 1007-1013 (1998).
Sugimura, T. in Recent Research Developments in Organic Chemistry Vol. 2 (ed S. G. Pandalai) 47-53 (Transworld Research Network, 1998).
A Substrate Specific Chiral Modifier Activation on Enantio-differentiating Hydrogenation over Tartaric Acid-Modified Raney Nickel. Nakagawa, S., Sugimura, T. & Tai, A. Chem. Lett., 1257-1258 (1998).
Stereochemical study on cyclic acetal formation during anodic oxidation of naphthalene derivatices by transformation of chiral alcohol to ahiral acetal. Fujita, M., Ohshiba, M., Shioyama, S., Sugimura, T. & Tai, A. Chem. Commun., 2243-2244 (1998).

1997

Axial Chirality Control by 2,4-Pentanediol or Its Analog As a Simple Chiral Linking Bridge. Highly Diastereodifferentiating Homo-Coupling of 1-Lithio-2-Naphthyl Ether. Sugimura, T., Yamada, H., Inoue, S. & Tai, A. Tetrahedron: Asymmetry 8, 649-655 (1997).
Radical Reaction of the Dimethacrylic Ester of (2R,4R)-Pentanediol. Addition-Cyclization-Termination Process of High Yield under Rigorous Stereocontrol of the Termination Step. Sugimura, T., Nagano, S. & Tai, A. Tetrahedron Lett. 38, 3547-3548 (1997).
Asymmetric Baeyer-Villiger Reaction: Diastereodifferentiating Peracid Oxidation of Chiral Acetal in the Presence of Lewis Acid. Sugimura, T., Fujiwara, Y. & Tai, A. Tetrahedron Lett. 38, 6019-6022 (1997).
Stereodifferentiating Reaction by Using 2,4-Pentanediol as a Chiral Linking Bridge. Developement of Simple and Reliable Asymmetric Reactions. Sugimura, T. J. Synth. Org. Chem. Jpn. 55, 517-523 (1997).
Almost Perfect Enantio-differentiating Hydrogenation of Methyl 3-Cylcopropyl-3-oxopropanoate over Tartaric Acid Midified Raney Nickel Catalyst. Nakagawa, S., Sugimura, T. & Tai, A. Chem. Lett., 859-860 (1997).
Diastereo-differentiating Intramolecular Cyclopropanations of Prochiral Olefins and a Diazo Ester Linked by Optically Active 2,4-Pentanediol. Mori, A., Sugimura, T. & Tai, A. Tetrahedron: Asymmetry 8, 661-664 (1997).
Reliable Chiral Transfer through Thermodynamic Equilibrium of the Intramolecular Meerwein-Ponndorf-Varley Reduction and Oppenauer Oxidation. Fujita, M., Takarada, Y., Sugimura, T. & Tai, A. J. Chem. Soc., Chem. Commun., 1631-1632 (1997).

1996

Stereochemical Studies of the Enantio-differentiating Hydrogenation of Various Prochiral Ketones over Tartaric Acid-Modified Nickel Catalyst. Sugimura, T., Osawa, T., Nakagawa, S., Harada, T. & Tai, A. Stud. Surf. Sci. Catal. 101, 231-238 (1996).
A Stereochemical Study of the Isomerization of Cyclopropyl Ethers to Allyl Ethers Catalyzed with Zinc Iodide. Sugimura, T. et al. J. Org. Chem. 61, 6100-6103 (1996).
Enantiospecific Preparation of gem-Dimethylcyclopropane Fused Cycloheptanes via Valence Tautomerization of 3,4-Hometropilidene under Thermodynamic and Kinetic Control. Sugimura, T., Futagawa, T., Katagiri, T., Nishiyama, N. & Tai, A. Tetrahedron Lett. 37, 7303-7306 (1996).

1995

Some Preparation Methods of Tricyclo[4.1.0.02,7]hept-4en-3-one skeleton. Wakabayashi, S., Saito, N., Sugihara, Y., Sugimura, T. & Murata, I. Synthetic Commun. 25, 2019-2027 (1995).
Cyclopenta[a]phenalen-9(8H)-one: An Extended Phenalenone System. Sugihara, Y. et al. J. Chem. Soc., Perkin Trans. I, 2813-2816 (1995).

1994

Improved Asymmetrically Modified Nickel Catalyst Prepared from Ultrasonicated Raney Nickel. Tai, A. et al. Bull. Chem. Soc. Jpn. 67, 2473-2477 (1994).
Total Syntheses of (+)-Ipomeamarone and (-)-Ngaione via Novel Intramolecular Hydrogen Abstraction. Sugimura, T., Tai, A. & Koguro, K. Tetrahedron 50, 11647-11658 (1994).
Regio- and Diastereo-Chemically Controlled Photocycloaddition of a Arene and a Alkene Linked by a Chiral Auxiliary. Sugimura, T., Nishiyama, N., Tai, A. & Hakushi, T. Tetrahedron: Asymmetry 5, 1163-1166 (1994).

1993

Diastereoface Differentiating Peracid Oxidation of the Enol Ether Derived from Cyclohexanone and 2,4-Pentanediol: Preparation of Optically Pure 2-Hydroxycyclkohexanone Acetal. Sugimura, T., Nishiyama, N. & Tai, A. Tetrahedron: Asymmetry 4, 43-44 (1993).
Total Syntheses of (+)-Ipomeamarone and (-)-Ngaione. Sugimura, T., Koguro, K. & Tai, A. Tetrahedron Lett. 34, 509-512 (1993).
Intramolecular Hydrogen Shift in Reduction of β-Mercuro Ketal. Preparation of Optically Active sec-tert-1,3-diols. Sugimura, T. et al. Tetrahedron Lett. 34, 505-508 (1993).
Syntheis and Properties of 6-Dimethylaminotricyclo[5.3.0.02,5]deca-3,6,8,10-tetraene (6-Dimethylamino Dewer Azulene). Sugihara, Y. & Sugimura, T. Chem. Lett., 785-788 (1993).

1992

Synthesis and Field Test of a Pheromone Mimic of the Pine Sawfly (Neodiprion sertifer). Tai, A. et al. Biosci. Biotech. Biochem. 56, 1711-1714 (1992).
Methyl Carbenoid Addition to Enol Ethers Carrying a Chiral Auxiliary. Stereocontrol of Three Chiral Centers on Cyclopropyl Ether. Sugimura, T., Katagiri, T. & Tai, A. Tetrahedron Lett. 33, 367-368 (1992).
Mechanism of Isomerization of Cyclopropyl Ether with Zinc Iodide. New Synthetic Route of Optically Active Allyl Alcohols. Sugimura, T., Futagawa, T., Ryu, I. & Tai, A. J. Chem. Soc., Chem. Commun., 324-325 (1992).

1991

Highly Efficient Enantio-differentiating Hydrogenation over an Ultrasonicated Raney Nickel Catalyst Modified with Tartaric Acid. Tai, A. et al. J. Chem. Soc., Chem. Commun., 795-796 (1991).
Conformation in Solution of the Fully Toxic Domain of Heat-Stable Enterotoxin(STp) Produced by Enterotoxigenic Escherichia coli. Ozaki, H. et al. Bull. Chem. Soc. Jpn. 64, 1136 (1991).

1990

Diastereo-Differentiating Isomerization of Meso 3,4-Epoxycyclopentanone Ketal to a Chiral 4-Hydroxy-2-cyclopentenone Ketal. Yoshikawa, M., Sugimura, T. & Tai, A. Chem. Lett., 1003 (1990).
Structure-Activity Relationship of Escherichica coli Heat-Stable Enterotoxin: Role of Ala Residue at Position 14 in Toxin-Receptor Interaction. Yamasaki, S. et al. Bull. Chem. Soc. Jpn. 63, 2063 (1990).
Preparation of Stereochemically Pure Sex Pheromone Compornents of the Pine Sawfly (Neodiplion sertifer) and Field Tests of the Synthetic Compounds. Tai, A. et al. Agric. Biol. Chem. 54, 1753 (1990).
Asymmetrically modified Raney nickel catalyst (MRNi). Preparation of highly activve new catalyst and its applications. Tai, A., Kikukawa, T., Sugimura, T., Inoue, Y. & Osawa, T. Shokubai 32, 362-363 (1990).
Preparation of Optically Pure (3S,5S)- and (3R,5R)-2,6- Dimethyl-3,5-heptanediol. Sugimura, T., Yoshikawa, M., Yoneda, T. & Tai, A. Bull. Chem. Soc. Jpn. 63, 1080 (1990).
Diastereo-Differentiating Cyclopropanation of a Chiral Enol Ether: A Simple Method for the Preparation of Optically Pure Cyclopropyl Ethers. Sugimura, T., Yoshikawa, M., Futagawa, T. & Tai, A. Tetrahedron 46, 5955-5966 (1990).
Regio- and Stereo-controlled Cyclopropanation of Unsaturated Enol Ether. Sugimura, T., Futagawa, T. & Tai, A. Chem. Lett., 2291 (1990).
Synthetic Approach for (+)-Africanol. Sugimura, T., Futagawa, T. & Tai, A. Chem. Lett., 2295 (1990).
Conformation of a Peptide Formed by Unnatural Folding of Heat-Stable Enterotoxin of Enterotoxigenic Escherichia Coli. Hidaka, Y. et al. Peptide Chemistry, 321 (1990).

1989

Pahutoxine: Synthesis and Determination of Its Absolute Configuration. Yoshikawa, M., Sugimura, T. & Tai, A. Agri. Biol. Chem. 53, 37 (1989).
Diastereo-Differentiating Simmons-Smith Reaction Using A New Chiral Auxiliary. Sugimura, T., Futagawa, T., Yoshikawa, M. & Tai, A. Tetrahedron Lett. 30, 3807 (1989).
Unusual Thermal Behavior of Tricyclo[4.1.0.02,7]hept-4-en-3-one (Tropovalene). Sugihara, Y., Sugimura, T., Saito, N. & Murata, I. J. Chem. Soc., Chem. Commun., 537 (1989).

1988

Asymmetrically Modified Nickel Catalyst. Tai, A., Harada, T., Tsukioka, K., Osawa, T. & Sugimura, T. Proc. 9th. Int. Congr. Catal. Calgaly, 1082 (1988).
Diastereo-Differentiating Simmons-Smith Reaction Using 2,4-Pentanediol as A Chiral Auxilialy. Sugimura, T., Futagawa, T. & Tai, A. Tetrahedron Lett. 29, 5775-5778 (1988).

1987

Enantiospecific Total Synthsis of the Sesquiterpene Antibiotic (-)-Punctatin A and (+)-Punctatin D. Sugimura, T. & Paquette, L. A. J. Am. Chem. Soc. 109, 3017 (1987).
The Preparation of Optically Pure 3-Hydoroxybutanoic acid and its Homologues as the Dibenzylammoniumsalt. Kikukawa, T., Iizuka, Y., Sugimura, T., Harada, T. & Tai, A. Chem. Lett., 1267-1270 (1987).

1986

Valence Isomers of Azulene and Heptalene. Sugihara, Y., Sugimura, T., Wakabayashi, S. & Murata, I. Tetrahedron 42, 1745 (1986).
Enantiospecific Total Synthesis and Absolute Configulational Assignment of (-)-Punctatin A (antibiotic M95464). Paquette, L. A. & Sugimura, T. J. Am. Chem. Soc. 108, 3841 (1986).

1984

Parent Azulvalene and Dewar Azulen. Syntheses and isomerizations of Tetracyclo[5.3.0.02,4.03,5]deca-6,8,10-triene and Tricyclo[5.3.0.02,5]deca-3,6,8,10-triene. Sugihara, Y., Sugimura, T. & Murata, I. J. Am. Chem. Soc. 106, 7268 (1984).

1983

Synthesis of 3a,8a-Dihydrocyclopent[a]inden-3(8H)-one. Sugihara, Y., Sugimura, T. & Murata, I. Bull. Chem. Soc. Jpn. 56, 2859-2860 (1983).

1982

Synthesis and Termal Behavior of 6-Methoxytricyclo-[5.3.0.02,5]deca-3,6,8,10-tetraene (Methoxy-Dewar- Azulene). Similarity between Valence Isomers of Azulen and Benzene. Sugihara, Y., Sugimura, T. & Murata, I. J. Am. Chem. Soc. 104, 2495-2496 (1982).
Valence Isomers of Cyclic Conjugated Compounds. Sugihara, Y. & Sugimura, T. Yuukigouseikagakukyoukaishi 40, 629-641 (1982).

1981

Valence Isomer of 4-Methoxyazulene. Synthesis of 6-Methoxytetracyclo[5.3.0.02,4.03,5]deca-6,8,10-triene. Sugihara, Y., Sugimura, T. & Murata, I. J. Am. Chem. Soc. 103, 6738-6739 (1981).

1980

Synthesis of 9,10-Benzotetracyclc[5.3.0.02,4.03,5]deca-1(7),9-dien-6-one. A Valence Isomer of Benz[a]azulen-9-(10H)-one. Sugihara, Y., Sugimura, T. & Murata, I. Chem. Lett., 1103-1106 (1980).