Total synthesis of (±)-lepadiformine via an amidoacrolein cycloaddition

被引：60

作者：

Greshock, TJ ^{[1
]}

Funk, RL ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 22期

关键词：

D O I：

10.1021/ol0165903

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The total synthesis of the cytotoxin lepadiformine is described. The intermolecular cycloaddition of a 2-amidoacrolein with the dimethyl acetal of 4,6-heptadienal gave a cycloadduct that was strategically functionalized for elaboration of the tricyclic ring system. These steps include a diastereoselective addition of an organoytterbium reagent to an aidehyde, cyclization to the trans-perhydroquinoline substructure via a Mitsunobu reaction, and an iodine-promoted amine cyclization with an alkene to introduce the pyrrolidine ring.

引用

页码：3511 / 3514

页数：4

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