Enantioselective allyltitanation. Application to the synthesis of lactone units related to compactin and mevinolin

被引：20

作者：

Bouzbouz, S ^{[1
]}

Cossy, J ^{[1
]}

机构：

[1] ESPCI, CNRS, Chim Organ Lab, F-75231 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 18期

关键词：

allyltitanation; 1,3-diols; lactones; compactin; mevinolin;

D O I：

10.1016/S0040-4039(00)00451-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective convergent synthesis of two different models of the lactone units of compactin and mevinolin was achieved using two consecutive enantioselective allyltitanations of aldehydes. (C) 2000 Elsevier Science Ltd, All rights reserved.

引用

页码：3363 / 3366

页数：4

共 25 条

[1] SYNTHESIS OF OPTICALLY-ACTIVE T-BUTYL (3R,5S)-3,5-ISOPROPYLIDENEDIOXY-6-HEPTYNOATE THROUGH BAKERS-YEAST REDUCTION OF METHYL 3-OXO-4-PENTYNOATE [J].

ANSARI, MH ;

KUSUMOTO, T ;

HIYAMA, T .

TETRAHEDRON LETTERS, 1993, 34 (51) :8271-8274

[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] STUDIES ON ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY-DELTA-LACTONE INHIBITORS OF HMGCOA REDUCTASE .1. A NEW PREPARATION OF THE LACTONE MOIETY OF COMPACTIN [J].

BONADIES, F ;

DIFABIO, R ;

GUBBIOTTI, A ;

MECOZZI, S ;

BONINI, C .

TETRAHEDRON LETTERS, 1987, 28 (06) :703-706

[4] Enantioselective synthesis of syn- and anti-1,3-diols via allyltitanation of unprotected β-hydroxyaldehydes [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2000, 2 (04) :501-504

[5] CRYSTAL AND MOLECULAR-STRUCTURE OF COMPACTIN, A NEW ANTIFUNGAL METABOLITE FROM PENICILLIUM-BREVICOMPACTUM [J].

BROWN, AG ;

SMALE, TC ;

KING, TJ ;

HASENKAMP, R ;

THOMPSON, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (11) :1165-1173

[6]

CLEEMAN JI, 1988, ARCH INTERN MED, V148, P36, DOI 10.1001/archinte.148.1.36

[7] MONACOLIN-K, A NEW HYPOCHOLESTEROLEMIC AGENT PRODUCED BY A MONASCUS SPECIES [J].

ENDO, A .

JOURNAL OF ANTIBIOTICS, 1979, 32 (08) :852-854

[8] ML-236A, ML-236B, AND ML-236C, NEW INHIBITORS OF CHOLESTEROGENESIS PRODUCED BY PENICILLIUM CITRINUM [J].

ENDO, A ;

KURODA, M ;

TSUJITA, Y .

JOURNAL OF ANTIBIOTICS, 1976, 29 (12) :1346-1348

[9] STEREOSELECTIVE SYNTHESIS OF THE TETRASUBSTITUTED CYCLOHEXANE CORE OF A MONOCYCLIC MEVINIC ACID ANALOG [J].

ERMOLENKO, MS ;

OLESKER, A ;

LUKACS, G .

TETRAHEDRON LETTERS, 1994, 35 (05) :711-714

[10] TOTAL SYNTHESIS OF A MONOCYCLIC ANALOG OF COMPACTIN [J].

ERMOLENKO, MS ;

OLESKER, A ;

LUKACS, G .

TETRAHEDRON LETTERS, 1994, 35 (05) :715-718

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