Studies toward (-)-peduncularine

ORGN 758

David M. Hodgson, david.hodgson@chem.ox.ac.uk and Ruth E. Shelton. Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom
Peduncularine is an alkaloid first isolated in 1971 and is known to have some cytotoxic activity against human breast cancer cells. It contains an unusual 6-azabicyclo[3.2.1]oct-3-ene core which, as we envisaged, can be assembled from known epoxytropinone (1) (2 steps from N-alkoxycarbonyl pyrrole) using a novel cascade process to generate racemic ketone (2).