Brief, efficient and highly diastereoselective synthesis of (±)-pumiliotoxin C based on the generation of an octahydroquinoline precursor via a four-component reaction†
Swarupananda Maiti,J. Carlos Menéndez
Chemical Communications Pub Date : 05/06/2011 00:00:00 , DOI:10.1039/C1CC11246E
Abstract

A short and highly diastereoselective synthesis of the amphibian alkaloid pumiliotoxin C is described, based on the preparation of an octahydroquinoline derivative through a four-component reaction. The route proceeds in 66% overall yield from 1,3-cyclohexanedione and includes two hydrogenation steps, whose stereochemical outcome was controlled vianitrogen acylation.

Graphical abstract: Brief, efficient and highly diastereoselective synthesis of (±)-pumiliotoxin C based on the generation of an octahydroquinoline precursor via a four-component reaction