Palladium-catalyzed enantioselective desymmetrization for the total synthesis of hodgkinsine and related structures

ORGN 743

Matthew J. Durbin, ch0mjd@bath.ac.uk and Michael C. Willis, m.c.willis@bath.ac.uk. Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom
The application of an enantioselective Suzuki desymmetrisation as the key transformation in the total synthesis of naturally occurring alkaloids is described. The design of a suitable boronic substrate and its subsequent coupling with a range of functionalized meso-chimonanthines (I) to yield optically active hodgkinsine (II) is being investigated. As well as application to the desymmetrisation of meso compounds, this methodology is expected to be applicable to other achiral substrates such as calycanthine to furnish calycosidine (III).