An efficient synthesis of optically active metabolites of platelet adhesion inhibitor OPC-29030 by lipase-catalyzed enantioselective transesterification

被引：16

作者：

Kitano, K ^{[1
]}

Matsubara, J ^{[1
]}

Ohtani, T ^{[1
]}

Otsubo, K ^{[1
]}

Kawano, Y ^{[1
]}

Morita, S ^{[1
]}

Uchida, M ^{[1
]}

机构：

[1] Otsuka Pharmaceut Co Ltd, Tokushima Res Inst, Tokushima 7710192, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(99)00946-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The optically active metabolites of (S)-3,4-dihydro-6-[3-(1-o-tolyl-2-imidazolyl)sulfinylpropoxy]-2(1H)-quinolinone (OPC-29030, 1), which is a new anti-platelet agent (platelet adhesion inhibitor), were effectively synthesized by the enzyme-catalyzed enantioselective transesterification of the racemic sulfinyl metabolites. The enzymes can recognize a stereogenic sulfur atom remote fi om the reaction site. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5235 / 5238

页数：4

共 50 条

[41] Preparation of optically active trifluoromethylated (3′-indolyl) thiacarboxylic acids, novel plant growth regulators, through lipase-catalyzed enantioselective hydrolysis
Kato, K
Tanaka, S
Fujii, S
Katayama, M
Kimoto, H
JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 1999, 87 (01) : 76 - 81
[42] Facile synthesis of optically active γ-lactones via lipase-catalyzed reaction of 4-substituted 3-hydroxybutyramides
Matsumura, Y
Endo, T
Chiba, M
Fukawa, H
Terao, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 2000, 48 (02) : 304 - 305
[43] Chemoenzymatic Asymmetric Synthesis of Optically Active Pentane-1,5-diamine Fragments by Means of Lipase-Catalyzed Desymmetrization Transformations
Rios-Lombardia, Nicolas
Busto, Eduardo
Gotor-Fernandez, Vicente
Gotor, Vicente
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (14): : 5709 - 5718
[44] Synthesis of optically active novel 1,1,2-trifluoro-1-alken-3-ols through lipase-catalyzed reaction
Takagi, Y
Kashiwagi, M
Kihara, H
Itoh, T
TETRAHEDRON LETTERS, 1999, 40 (14) : 2801 - 2802
[45] LIPASE-CATALYZED SYNTHESIS OF OPTICALLY-ACTIVE N,N,N,-TRIMETHYLETHANAMINIUM, ALPHA-TOCOPHEROL ANALOG MDL-73404
MIZUGUCHI, E
SUZUKI, T
ACHIWA, K
SYNLETT, 1994, (11) : 929 - 930
[46] LIPASE-CATALYZED KINETIC RESOLUTION WITH INSITU RACEMIZATION - ONE-POT SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRIN ACETATES FROM ALDEHYDES
INAGAKI, M
HIRATAKE, J
NISHIOKA, T
ODA, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9360 - 9361
[47] Efficient synthesis of optically pure 1,1,1-trifluoro-2-alkanols through lipase-catalyzed acylation in organic media
Hamada, H
Shiromoto, M
Funahashi, M
Itoh, T
Nakamura, K
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07): : 2332 - 2336
[48] ASYMMETRIC-SYNTHESIS OF A CHIRAL NORBORNENE DERIVATIVE BY LIPASE-CATALYZED TRANSESTERIFICATION OF CIS-ENDO-5-NORBORNENE-2,3-DIMETHANOL AND ITS APPLICATION TO THE SYNTHESIS OF AN OPTICALLY-ACTIVE TXA2 ANTAGONIST
MURATA, M
IKOMA, S
ACHIWA, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (08) : 2329 - 2331
[49] Asymmetric synthesis of 5,6-dehydrosenedigitalene using lipase-catalyzed highly enantioselective transesterification of a primary alcohol with vinyl 3-(4-trifluoromethylphenyl)propanoate
Kawasaki, M
Hayashi, Y
Kakuda, H
Toyooka, N
Tanaka, A
Goto, M
Kawabata, S
Kometani, T
TETRAHEDRON-ASYMMETRY, 2005, 16 (24) : 4065 - 4072
[50] Synthesis of optically active partly gem-difluorinated allylic alcohols via [2,3]-Wittig rearrangements and lipase-catalyzed reaction
Itoh, T
Kudo, K
Tanaka, N
Sakabe, K
Takagi, Y
Kihara, H
TETRAHEDRON LETTERS, 2000, 41 (23) : 4591 - 4595

← 1 2 3 4 5 →