Total synthesis of (-)-indolizidine 167B via an unusual Wolff rearrangement from an α,β-unsaturated diazoketone

被引：29

作者：

Pinho, Vagner D. ^{[1
]}

Burtoloso, Antonio C. B. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 07期

基金：

巴西圣保罗研究基金会;

关键词：

Indolizidine alkaloids; Unsaturated diazoketones; Wolff rearrangement; Arndt-Eistert homologation; Photochemical; INDOLIZIDINE ALKALOIDS; QUINOLIZIDINE;

D O I：

10.1016/j.tetlet.2011.12.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of the (-)-indolizidine alkaloid 167B and two formal syntheses of (-)-indolizidine 209D and (-)-coniceine are described in just three steps from an alpha,beta-unsaturated diazoketone, via an unusual photochemical Wolff rearrangement. Preparation of the unsaturated diazoketone is straightforward from N-Cbz-prolinal and a 3-diazo-2-oxopropylphosphonate, employing a Horner-Wadsworth-Emmons reaction. The strategy should be feasible and easily adaptable to the synthesis of other indolizidine alkaloids and analogues. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：876 / 878

页数：3

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