An expeditious synthesis of nocardiolactone

被引：11
|
作者：
Sun, YP [1 ]
Wu, YK [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
SYNLETT | 2005年 / 09期
关键词：
asymmetric synthesis; chiral auxiliaries; lactones; ring contractions; total synthesis;
D O I：
10.1055/s-2005-869832
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nocardiolactone was synthesized by using a Crimmins asymmetric aldolization followed by a DMAP-mediated removal of the auxiliary with concurrent protection of the carboxylic group as a benzyl ester, activation of the beta-hydroxyl group as a mesylate, hydrogenolysis of the benzyl ester, and a novel DBU-mediated lactonization that converted the syn-configuration to the trans one.
引用
收藏
页码：1477 / 1479
页数：3
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