高价碘(III)介导的炔丙基胍的级联环化反应及凯阿里宁 B 和 C 的全合成。

Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C.

机构信息

Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, Belgium.

Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya street, Moscow, 117198, Russia.

出版信息

Chemistry. 2017 Apr 19;23(22):5224-5227. doi: 10.1002/chem.201700934. Epub 2017 Mar 29.

DOI:10.1002/chem.201700934

PMID:28263005

Abstract

An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental results.

摘要

发展了一种由苯碘二乙酸（PIDA）促进的炔丙基胍的氧化级联环化反应。该方案为生物碱 kealiinines B 和 C 及其同系物的合成提供了一条有效的途径。乙炔取代基的电子性质的差异导致了两种环化方式。根据实验结果提出了一个合理的机制。