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Issue 1, 2007

Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (−)-aphanorphine

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Abstract

A full account of studies which led to the efficient asymmetric synthesis of (−)-aphanorphine 1 is reported. Two routes to the key cyclic sulfamidate intermediate 5 are described, the first was based on a chiral auxiliary approach and the second utilised asymmetric hydrogenation methodology. A range of C(3)-substituted lactams (4, 22 and 25) were synthesised and evaluated as precursors for Pd(0) catalysed entries (based on (i) α-arylation of a lactam enolate and (ii) reductive Heck reaction) to the 3-benzazepine core of 1. These approaches were less effective than an aryl radical cyclisation which allowed the completion of a synthesis of 1 in 12 steps from anisaldehyde.

Graphical abstract: Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (−)-aphanorphine

Article information


Submitted
16 Oct 2006
Accepted
31 Oct 2006
First published
16 Nov 2006

Org. Biomol. Chem., 2007,5, 143-150
Article type
Paper

Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (−)-aphanorphine

J. F. Bower, P. Szeto and T. Gallagher, Org. Biomol. Chem., 2007, 5, 143 DOI: 10.1039/B614999E

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