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

被引：60

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

页码：1244 / 1247

页数：4

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