A synthetic approach to (+/-)-forskolin .1. Preparation of key hydrobenzofuran intermediates

被引：0

作者：

Anies, C ^{[1
]}

Pancrazi, A ^{[1
]}

Lallemand, JY ^{[1
]}

机构：

[1] ECOLE POLYTECH,DCSO,CNRS,ORGAN SYNTH LAB,F-91128 PALAISEAU,FRANCE

来源：

BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1997年 / 134卷 / 02期

关键词：

forskolin; tributylstannane; radical cyclization; transmetallation; vinylstannane; vinyl iodide; Pd(0) coupling reaction;

D O I：

暂无

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In a synthetic approach to (+/-)-forskolin 1, a stereoselective preparation of the unsaturated lactone 2 was: envisaged. Propargylic derivatives 18a-c were prepared from available alpha-ionone 5 and treated with Bu3SnH/AIBN to give the bicyclic vinylstannanes 19a-c in high yield. From these compounds we then performed transmetallation reactions to obtain the 21a-c and 22b homologous derivatives. The two enyne compounds 29 and 30 were then prepared by our previous approach to lactone 2 involving a radical C7-C8 bond formation. In a second radical approach promoted by SmI2, the diol 10, was used to synthesize a potential precursor of the dialdehyde 9.

引用

页码：183 / 202

页数：20

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