Microbiological transformations .31. Synthesis of enantiopure epoxides and vicinal diols using fungal epoxide hydrolase mediated hydrolysis.

被引:15
作者
PedragosaMoreau, S [1 ]
Archelas, A [1 ]
Furstoss, R [1 ]
机构
[1] FAC SCI LUMINY,GRP BIOCATALYSE & CHIM FINE,F-13288 MARSEILLE 9,FRANCE
关键词
D O I
10.1016/0040-4039(96)00540-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective hydrolysis of epoxyindene and dihydronaphtalene epoxides by the fungus Beauveria sulfurescens (ATCC 7159) is described. This allowed the preparation of both these epoxides, as well as of the corresponding diols, in good to excellent enantiomeric purity. (C) 1996 Published by Elsevier Science Ltd
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收藏
页码:3319 / 3322
页数:4
相关论文
共 18 条
[1]   SYNTHESIS OF (+)-NAPHTHALENE AND (-)-NAPHTHALENE AND ANTHRACENE 1,2-OXIDES [J].
AKHTAR, MN ;
BOYD, DR ;
HAMILTON, JG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (10) :2437-2440
[2]   CHEMICAL SYNTHESIS AND OPTICAL PURITY DETERMINATION OF OPTICALLY-ACTIVE 1,2-EPOXYINDAN AND ALCOHOL PRODUCTS WHICH ARE ALSO DERIVED FROM MAMMALIAN OR MICROBIAL-METABOLISM OF INDENE OR INDANONES [J].
BOYD, DR ;
SHARMA, ND ;
SMITH, AE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11) :2767-2770
[3]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[4]   THREITOL-STRAPPED MANGANESE PORPHYRINS AS ENANTIOSELECTIVE EPOXIDATION CATALYSTS OF UNFUNCTIONALIZED OLEFINS [J].
COLLMAN, JP ;
LEE, VJ ;
KELLENYUEN, CJ ;
ZHANG, XM ;
IBERS, JA ;
BRAUMAN, JI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) :692-703
[5]   CATALYTIC ASYMMETRIC OXIDATIONS USING OPTICALLY-ACTIVE (SALEN)MANGANESE(III) COMPLEXES AS CATALYSTS [J].
KATSUKI, T .
COORDINATION CHEMISTRY REVIEWS, 1995, 140 :189-214
[6]   A CONVERGENT SYNTHESIS NOVEL CONFORMATIONALLY RESTRICTED HIV-1 PROTEASE INHIBITORS [J].
KIM, BM ;
GUARE, JP ;
HANIFIN, CM ;
ARFORDBICKERSTAFF, DJ ;
VACCA, JP ;
BALL, RG .
TETRAHEDRON LETTERS, 1994, 35 (29) :5153-5156
[7]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[8]   KINETIC RESOLUTION OF 1,2-DIHYDRONAPHTHALENE OXIDE AND RELATED EPOXIDES VIA ASYMMETRIC C-H HYDROXYLATION [J].
LARROW, JF ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12129-12130
[9]  
PALUCKI M, 1995, TETRAHEDRON LETT, V36, P5457
[10]  
Pedragosa-Moreau S, 1994, Bioorg Med Chem, V2, P609, DOI 10.1016/0968-0896(94)85008-9