Discoipyrrole D 的全合成。

A Total Synthesis of the Marine Alkaloid Discoipyrrole D.

机构信息

Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.

出版信息

J Org Chem. 2017 Sep 15;82(18):9328-9334. doi: 10.1021/acs.joc.7b01192. Epub 2017 Aug 31.

DOI:10.1021/acs.joc.7b01192

PMID:28809491

Abstract

A total synthesis of the diastereoisomeric pair of compounds, 4, assigned to the marine alkaloid discoipyrrole D is reported. A series of palladium-catalyzed cross-coupling and other reactions was employed to assemble the relevant 1,2,3,4-tetrasubstituted pyrrole (16) that was engaged in MoOPH-mediated oxidative cyclization, then conjugate addition, and redox processes to complete the synthesis. This work serves to confirm the structure (4) originally assigned to discoipyrrole D.

摘要

本文报道了海洋生物碱 discoipyrrole D 的非对映异构体对 4 的全合成。采用了一系列钯催化的交叉偶联和其他反应，来组装相关的 1,2,3,4-四取代吡咯（16），然后进行 MoOPH 介导的氧化环化、共轭加成和氧化还原过程，完成了合成。这项工作证实了最初分配给 discoipyrrole D 的结构（4）。