AN ALTERNATIVE APPROACH TO MEVINIC ACID ANALOGS FROM METHYL (3R)-(-)-3-HYDROXYHEX-5-ENOATE AND AN EXTENSION TO UNAMBIGUOUS SYNTHESES OF (6R)-(+)-GONIOTHALAMIN AND (6S)-(-)-GONIOTHALAMIN

被引：24

作者：

BENNETT, F

KNIGHT, DW

FENTON, G

机构：

[1] CHEM DEPT, UNIV PK, NOTTINGHAM NG7 2RD, ENGLAND

[2] RHONE POULENC RORER LTD, CENT RES, DAGENHAM RM10 7XS, ESSEX, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 03期

关键词：

D O I：

10.1039/p19910000519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ozonolysis of the 3-silyloxyhexenoate 12, derived from the yeast reduction product methyl (3R)-(-)-3-hydroxyhex-5-enoate 6 and having an enantiomeric enrichment of 78%, followed by Wittig homologation and selenolactonization leads to the unsaturated mevinic acid analogues 17 and 18. Subsequent dehydration gives both enantiomers of the natural product goniothalamin 20 and 21.

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页码：519 / 523

页数：5

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