A new synthetic approach to forskolin: Construction of the ABC ring system from D-galactose

被引：15
作者：
Hanna, I
Wlodyka, P
机构：
[1] Lab. de Synt. Organique A., Ecole Polytechnique
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 20期
关键词：
D O I：
10.1021/jo970999h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular Diels-Alder reaction of dienyne 14 afforded naphthopyran 18 which underwent 1,4-addition of methyl copper reagent to give the functionalized tricyclic system of forskolin 17. The synthesis of dienyne 14 is based on a stereoselective introduction of carbon side chains at C(1) and C(2) of tri-O-acetyl-D-galactal via C-Ferrier followed by Claisen-Ireland rearrangements.
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页码：6985 / 6990
页数：6
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