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

Organic letters (2010-02-24)
Katherine M Bogle, David J Hirst, Darren J Dixon
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(Isopropenyloxy)trimethylsilane, ≥85%