A NEW PRENYLATION METHOD USING THE LITHIUM ENOLATE OF PRENAL - REACTION WITH POLYUNSATURATED ALDEHYDES - A SHORT ACCESS TO RETINAL

被引：12

作者：

DUHAMEL, L

GUILLEMONT, J

POIRIER, JM

CHABARDES, P

机构：

[1] IRCOF,F-76134 MONT ST AIGNAN,FRANCE

[2] CTR RECH CARRIERES,F-69192 ST FONS,FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 35期

关键词：

LITHIUM DIENOLATE; GAMMA-ADDITION; DIHYDROPYRANS; POLYUNSATURATED ALDEHYDES; PRENYLATION;

D O I：

10.1016/0040-4039(91)80022-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enolate of prenal 1 prepared from the corresponding silyl enol ether 2 or enol acetate 3 led to a gamma-regiospecific reaction with polyunsaturated aldehydes 4 yielding dihydropyrans 5 leading after hydrolysis to polyenals 7. This process allows the introduction of the isoprenyl skeleton. A synthesis of retinal from beta-ionylidenacetaldehyde is reported.

引用

页码：4499 / 4500

页数：2