克拉维菌素A、B和匹他霉素的全合成。

Total synthesis of clavepictines A and B and pictamine.

作者信息

Yu Shanghai, Pu Xiaotao, Cheng Tiejun, Wang Renxiao, Ma Dawei

机构信息

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

出版信息

Org Lett. 2006 Jul 20;8(15):3179-82. doi: 10.1021/ol060960b.

DOI:10.1021/ol060960b

PMID:16836360

Abstract

[Structure: see text] A short route for assembling clavepictines A and B and pictamine is described, which features elaboration of its trisubstituted piperidine moiety via condensation of a beta-keto sulfone with an l-alanine-derived bromide and subsequent alkylative cyclization and construction of its quinolizidine skeleton via a diastereoselective intramolecular conjugate addition. The possible stereochemical course for this conjugate addition is discussed.

摘要

[结构：见正文] 描述了一种合成克拉维菌素A、B和匹他霉素的短路线，其特点是通过β-酮砜与L-丙氨酸衍生的溴化物缩合，随后进行烷基化环化来构建其三取代哌啶部分，并通过非对映选择性分子内共轭加成构建其喹诺里西啶骨架。讨论了这种共轭加成可能的立体化学过程。