Transannular Diels-Alder studies on the asymmetric total synthesis of chatancin:: The pyranophane approach

被引：23

作者：

Toró, A ^{[1
]}

L'Heureux, A ^{[1
]}

Deslongchamps, P ^{[1
]}

机构：

[1] Univ Sherbrooke, Inst Pharmacol Sherbrooke, Organ Synth Lab, Sherbrooke, PQ J1H 5N4, Canada

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol006220z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A pathway is proposed for the biosynthesis of (+)-chatancin and (+)-sarcophytin linking these tetracycles to cembranoids by a pyranophane transannular Diels-Alder reaction. Preliminary synthetic results in this direction to reach macrocyclic dienedione 28 from farnesol are reported. Major synthetic steps include a Prins reaction, two enantioselective hydrogenations, and a macrocyclization via a beta-ketosulfoxide Michael-addition on an enone.

引用

页码：2737 / 2740

页数：4

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