ENANTIOSELECTIVE SYNTHESIS OF THE HYDROXYL-LACTONE MOIETY OF MEVINIC ACIDS

被引：21

作者：

MCCAGUE, R ^{[1
]}

OLIVO, HF ^{[1
]}

ROBERTS, SM ^{[1
]}

机构：

[1] UNIV EXETER,DEPT CHEM,EXETER EX4 4RJ,DEVON,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)79228-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Oxa-4endo-hydroxybicyclo[3.3.0]-oct-7-en-3-one was resolved with Pseudomonas fluorescens lipase and one of the enantiomers was converted into a key intermediate in the synthesis of mevinic acids.

引用

页码：3785 / 3786

页数：2

共 19 条

[1] SYNTHESES OF 4(R)-SILYLOXY-6(S)-IODOMETHYL-TETRAHYDROPYRAN-2-ONE AND ITS ENANTIOMER, BUILDING-BLOCKS FOR HMG-COA REDUCTASE INHIBITORS [J].

BAADER, E ;

BARTMANN, W ;

BECK, G ;

BERGMANN, A ;

FEHLHABER, HW ;

JENDRALLA, H ;

KESSELER, K ;

SARIC, R ;

SCHUSSLER, H ;

TEETZ, V ;

WEBER, M ;

WESS, G .

TETRAHEDRON LETTERS, 1988, 29 (21) :2563-2566

[2] METHYL (3R)-3-HYDROXYHEX-5-ENOATE AS A PRECURSOR TO CHIRAL MEVINIC ACID ANALOGS [J].

BENNETT, F ;

KNIGHT, DW ;

FENTON, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :133-140

[3] TOTAL SYNTHESIS OF DIHYDROMEVINOLIN AND A SERIES OF RELATED 3-HYDROXY-3-METHYLGLUTARYL COENZYME-A REDUCTASE INHIBITORS [J].

BLACKWELL, CM ;

DAVIDSON, AH ;

LAUNCHBURY, SB ;

LEWIS, CN ;

MORRICE, EM ;

REEVE, MM ;

ROFFEY, JAR ;

TIPPING, AS ;

TODD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5596-5606

[4]

CHAUDHARY SK, 1979, TETRAHEDRON LETT, P99

[5] TOTAL SYNTHESIS OF (+/-)-SESBANIMIDE-A AND (+/-)-SESBANIMIDE-B [J].

GRIECO, PA ;

HENRY, KJ ;

NUNES, JJ ;

MATT, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :368-370

[6] SYNTHETIC STUDIES ON THE MEVINIC ACIDS USING THE CHIRON APPROACH - TOTAL SYNTHESIS OF (+)-DIHYDROMEVINOLIN [J].

HANESSIAN, S ;

ROY, PJ ;

PETRINI, M ;

HODGES, PJ ;

DIFABIO, R ;

CARGANICO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5766-5777

[7]

JOHNSON WS, 1988, TETRAHEDRON LETT, V31, P3757

[8] MILD AND EFFICIENT METHODS FOR THE REDUCTIVE CLEAVAGE OF NITROGEN-OXYGEN BONDS [J].

KECK, GE ;

FLEMING, S ;

NICKELL, D ;

WEIDER, P .

SYNTHETIC COMMUNICATIONS, 1979, 9 (04) :281-286

[9] HETERO-DIELS-ALDER REACTION IN WATER - SYNTHESIS OF ALPHA-HYDROXY-GAMMA-LACTONES [J].

LUBINEAU, A ;

AUGE, J ;

LUBIN, N .

TETRAHEDRON LETTERS, 1991, 32 (51) :7529-7530

[10] CONVERSION OF (-)-4-HYDROXY-2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONE INTO THE ANTI-HIV AGENT CARBOVIR [J].

MACKEITH, RA ;

MCCAGUE, R ;

OLIVO, HF ;

PALMER, CF ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03) :313-314

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