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
收藏
页码：1543 / 1547
页数：5
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