TOTAL SYNTHESES OF NATURAL (+)-(4R,6R)-4-HYDROXY-6-PENTYLVALEROLACTONE AND OF (-)-(6R)-MASSOIALACTONE

被引：39

作者：

BENNETT, F

KNIGHT, DW

FENTON, G

机构：

[1] UNIV NOTTINGHAM,DEPT CHEM,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 / 06期

关键词：

D O I：

10.1039/p19910001543

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric total synthesis and hence a confirmation of the absolute configuration of naturally occurring (+)-(4R,6R)-4-hydroxy-6-pentylvalerolactone 10, a metabolite of Cephalosporium recifei, is described, starting from the yeast reduction product methyl (3R)-3-hydroxyhex-5-enoate 5. The key step is a highly trans-selective kinetic iodolactonization of the unsaturated acid 16e. Dehydration of the lactone 10 leads to natural (-)-(6R)-massoialactone 11.

引用

页码：1543 / 1547

页数：5

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