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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.765-777
Published online, 31st July, 2013
DOI: 10.3987/COM-13-S(S)39
Regio- and Stereoselective Derivatisation of an Aporphine Scaffold

Jonathan D. M. Atkinson, Stephen G. Davies,* and James E. Thomson

*Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.

Abstract

Treatment of 10,11-dimethoxyaporphine with chromium hexacarbonyl was found to give two diastereoisomeric products on regioselective co-ordination of the chromium tricarbonyl fragment to the A ring. For one of the diastereoisomeric complexes, alkylation was found to proceed with high regio- and diastereoselectivity at C(4), whereas regio- and diastereoselective alkylation was observed at C(6a) for the other diastereoisomer. In the case of the C(4)- and C(6a)-methylated products, these substrates were decomplexed in high yield to give the corresponding enantiopure, C(4)- and C(6a)-methyl substituted aporphines.