Development of a Strategy for the Asymmetric Synthesis of Polycyclic Polyprenylated Acylphloroglucinols via N-Amino Cyclic Carbamate Hydrazones: Application to the Total Synthesis of (+)-Clusianone

被引：53

作者：

Garnsey, Michelle R. ^{[1
]}

Lim, Daniel ^{[1
]}

Yost, Julianne M. ^{[1
]}

Coltart, Don M. ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 22期

基金：

美国国家科学基金会;

关键词：

GARSUBELLIN-A; BRIDGEHEAD LITHIATION; CLUSIANONE; (+/-)-CLUSIANONE; KETONES; BENZOPHENONES; DERIVATIVES; NEMOROSONE;

D O I：

10.1021/ol1022728

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A broadly applicable asymmetric synthetic strategy utilizing N-amino cyclic carbamate alkylation that provides access to the various stereochemical permutations of a common structural motif found in many polycyclic polyprenylated acylphloroglucinols is described. The utility of this methodology is demonstrated through the first asymmetric total synthesis of the antiviral agent (+)-clusianone.

引用

收藏

页码：5234 / 5237

页数：4

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