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
收藏
页码：876 / 878
页数：3
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