Organic Letters 2010-03-19

Total synthesis of (+/-)-powelline and (+/-)-buphanidrine.

Katherine M Bogle, David J Hirst, Darren J Dixon

Index: Org. Lett. 12(6) , 1252-4, (2010)

Full Text: HTML

Abstract

The total synthesis of (+/-)-powelline (13 linear steps in an overall yield of 6%) and (+/-)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling allowed direct construction of the key quaternary carbon-to-aryl bond in high yield allowing rapid access to the target alkaloids.