Total Synthesis of (+)-Sieboldine A

被引：74

作者：

Canham, Stephen M. ^{[1
]}

France, David J. ^{[1
]}

Overman, Larry E. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 23期

关键词：

PYRROLIDINE HOMOAZASUGARS; LYCOPODIUM; CYCLIZATIONS; ROUTE; ENTRY;

D O I：

10.1021/ja103666n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of (+)-sieboldine A was completed in 20 steps from readily available (3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (5). Key steps are as follows: (a) a pinacol-terminated 1,6-enyne cyclization reaction to form the cis-hydrindanone core (11 --> 12), (b) formation of the Spiro tetrahydrofuran ring by stereoselective DMDO oxidation of tricyclic dihydropyran intermediate 15, and (c) formation of the unprecedented N-hydroxyazacyclononane ring by cyclization of a thioglycoside precursor (18 --> 19).

引用

页码：7876 / +

页数：3

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