Total synthesis of 8-deoxyvernolepin utilizing manganese(III)-mediated radical cyclizations

ORGN 179

Shane G. Henry, sgh25@cam.ac.uk1, David G. Hulcoop, jwb1004@hermes.cam.ac.uk1, David C. Blakemore2, and Jonathan W. Burton, jonathan.burton@chem.ox.ac.uk1. (1) Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom, (2) Sandwich Chemistry, Pfizer Global Research and Development, Ramsgate Road, Sandwich, CT13 9NJ, United Kingdom
Manganese(III) acetate is a mild single electron oxidant that has been widely used in radical reactions in organic synthesis. Work in our group has involved utilising intramolecular manganese(III) mediated radical cyclisations to construct fused tricyclic lactones, providing the skeletal core of many sesquiterpenes such as 8-deoxyvernolepin. The radical substrate can be envisioned to derive from a Diels-Alder reaction followed by a palladium mediated allylic substitution.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006