Total Synthesis of (+)-Omphadiol

被引：49

作者：

Liu, Gang ^{[1
]}

Romo, Daniel ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 33期

关键词：

asymmetric synthesis; cyclopropanation; natural products; protecting group free; terpenoids; RING-CLOSING METATHESIS; TRICYCLIC-BETA-LACTONES; OLEFIN METATHESIS; ENANTIOSELECTIVE SYNTHESIS; 1,5-ASYMMETRIC INDUCTION; 8-MEMBERED RINGS; KETO ACIDS; SESQUITERPENES; (+/-)-AFRICANOL; CONSTRUCTION;

D O I：

10.1002/anie.201102289

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A smooth transition from (R)-carvone to a β-lactone and then to (+)-omphadiol characterizes the first total synthesis of this sesquiterpene, which was achieved in ten steps and 18 overall yield. All six contiguous stereogenic centers were introduced in a highly diastereoselective manner. Key steps include a nucleophile-promoted aldol lactonization, a single-pot, sequential intra-/intermolecular dialkylation, a tandem olefin isomerization/RCM, and a cyclopropanation with unusual facial selectivity. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7537 / 7540

页数：4

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