ORGN 431 |
Approaches to the total synthesis of Pestalotiopsin A
| Philip J. Calderwood and David J. Procter. Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, United Kingdom |
Pestalotiopsin A 1 is a sesquiterpene natural product isolated from the Pacific Yew tree Taxus brevifolia. Its unique oxatricyclic structure and its cytotoxic and immunosuppressive activity make it a challenging target for total synthesis. We have recently reported the first synthesis of the fully-functionalised bicylic core of Pestalotiopsin A. We will now describe our endeavours towards completion of the final, nine-membered carbocyclic ring. Two routes towards the completion of this ring will be described, both of which proceed via isoxazoline 2, formed by a 1,3-dipolar cycloaddition on lactone 3.  |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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