帕卡司他明（Jaspine B）、2-表帕卡司他明及其2-表吡咯烷类似物的实用合成

Practical Synthesis of Pachastrissamine (Jaspine B), 2-epi-Pachastrissamine, and the 2-epi-Pyrrolidine Analogue.

作者信息

Fujiwara Tomoya, Liu Bo, Niu Wenqi, Hashimoto Kazuki, Nambu Hisanori, Yakura Takayuki

机构信息

Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama.

出版信息

Chem Pharm Bull (Tokyo). 2016;64(2):179-88. doi: 10.1248/cpb.c15-00816.

DOI:10.1248/cpb.c15-00816

PMID:26833446

Abstract

The practical syntheses of pachastrissamine (jaspine B), 2-epi-pachastrissamine, and the 2-epimer of the pyrrolidine analogue were accomplished via the stereoselective reduction of an allylketone derived from commercially available diethyl D-tartrate and the cross-metathesis of an allyltetrahydrofuran or allypyrrolidine with 1-tridecene as key steps.

摘要

通过以市售的D -酒石酸二乙酯衍生的烯丙基酮的立体选择性还原以及烯丙基四氢呋喃或烯丙基吡咯烷与1 -十三碳烯的交叉复分解反应为关键步骤，实现了帕卡司他明（茉莉素B）、2 -表 -帕卡司他明及其吡咯烷类似物的2 -差向异构体的实际合成。