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对 (-)-limaspermidine 的对映选择性全合成和 (-)-1-乙酰基aspidoalbidine 的形式合成。

Enantioselective total synthesis of (-)-limaspermidine and formal synthesis of (-)-1-acetylaspidoalbidine.

机构信息

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University , Kunming 650091, People's Republic of China.

出版信息

J Org Chem. 2013 Nov 15;78(22):11444-9. doi: 10.1021/jo402004f. Epub 2013 Oct 29.

Abstract

Evolution of the synthetic strategy that culminated in the first asymmetric total synthesis of the Aspidosperma alkaloid limaspermidine is described. The successful enantioselective route to (-)-limaspermidine proceeds in 10 steps and with the isolation of only six intermediates using a Pd-catalyzed enantioselective decarboxylative allylation we have recently developed. This first enantioselective synthesis of (-)-limaspermidine establishes unambiguously its absolute configuration and allows the first asymmetric formal total synthesis of the Aspidoalbine alkaloid (-)-1-acetylaspidoalbidine.

摘要

描述了最终导致阿匹斯多玛烷生物碱利马培啶的首次不对称全合成的综合策略的演变。(-)-利马培啶的成功对映选择性路线经过 10 步,并且仅使用我们最近开发的 Pd 催化的对映选择性脱羧烯丙基化反应分离出六个中间体。(-)-利马培啶的首次对映选择性合成明确确定了其绝对构型,并允许(-)-1-乙酰阿匹多滨碱的第一个不对称全合成的阿匹多阿尔宾生物碱。

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