Concise, Stereocontrolled Synthesis of the Citrinadin B Core Architecture

被引：27

作者：

Guerrero, Carlos A. ^{[1
]}

Sorensen, Erik J. ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Frick Lab, Princeton, NJ 08544 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 19期

基金：

美国国家卫生研究院;

关键词：

TRYPTAMINE DERIVATIVES; CYCLIZATION; TRYPTOPHAN; OXIDATION;

D O I：

10.1021/ol2020362

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6-disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.

引用

页码：5164 / 5167

页数：4

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