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Flexible strategy for the synthesis of pyrrolizidine alkaloids. 2008
Timothy J Donohoe, and
Rhian E Thomas, and
Matthew D Cheeseman, and
Caroline L Rigby, and
Gurdip Bhalay, and
Ian D Linney
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom. timothy.donohoe@chem.ox.ac.uk
A general strategy for the production of pyrrolizidine alkaloids is described, starting from intermediate (+)-9. The key features are diastereoselective dihydroxylation, inversion at the ring junction by hydroboration of an enamine, and ring closure to form the bicyclo ring system. This route is attractive because of its brevity and versatility; four natural products were prepared with differing stereochemistry and substitution patterns. Finally, this work allowed assignment of the absolute stereochemistry of 2,3,7-triepiaustraline and hyacinthacine A 7.
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