A Tandem Prins/Schmidt Reaction Approach to Marine Alkaloids: Formal and Total Syntheses of Lepadiformines A and C

被引：58
|
作者：
Meyer, Angelica M. [1 ]
Katz, Christopher E. [1 ]
Li, Sze-Wan [1 ]
Velde, David Vander [1 ]
Aube, Jeffrey [1 ]
机构：
[1] Univ Kansas, Dept Med Chem, Struct Biol Ctr, Lawrence, KS 66047 USA
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 06期
基金：
美国国家卫生研究院;
关键词：
ASCIDIAN CLAVELINA-CYLINDRICA; COMPOSITE FUNCTIONAL-GROUP; SCHMIDT REACTION; EFFICIENT APPROACH; ALKYL AZIDES; CYCLIZATION; (+/-)-LEPADIFORMINE; (+/-)-STENINE; CONSTRUCTION; CARBOCYCLES;
D O I：
10.1021/ol100113r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.
引用
收藏
页码：1244 / 1247
页数：4
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