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
收藏
页码：2737 / 2740
页数：4
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