New approach to aphidicolin and total asymmetric synthesis of unnatural (11R)-(-)-8-epi-11-hydroxyaphidicolin by tandem transannular Diels-Alder/aldol reactions

被引：24

作者：

Bélanger, G ^{[1
]}

Deslongchamps, P ^{[1
]}

机构：

[1] CHU Sherbrooke, Inst Pharmacol, Dept Chim, Lab Synthese Organ, Sherbrooke, PQ J1H 5N4, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 21期

关键词：

D O I：

10.1021/jo0007635

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 8-epiaphidicolane skeleton (3) was formed in one key reaction by highly diastereoselective tandem transannular Diels-Alder (TADA)-aldol reactions from the trans-trans-cis trienic macrocycle (4). The unnatural derivative (11R)-(-)-8-epi-11-hydroxyaphidicolin (2) was thus constructed, and an original solution to the C16 functionalization problem of many aphidicolin (1) syntheses is presented.

引用

页码：7070 / 7074

页数：5

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