ORGN 481 |
Annonaceous acetogenins library: A bi-directional approach
| Sanjib Das, Lian-Sheng Li, and Subhash C. Sinha. The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 |
| Annonaceous acetogenins are known for their potent antitumour, antimalarial, immunosuppressive, pesticidal, and antifeedant activities. More than 350 acetogenins have been isolated from 37 species in the Annonaceae, a family of tropical trees and shrubs that accommodates over 2300 species. Most of these fatty acid derivatives exhibit very similar carbon skeletons with the main variations being the relative and absolute configuration of the various stereogenic oxygen functions. More than 40% of the annonaceous acetogenins contain two adjacent tetrahydrofuran rings flanked by two hydroxyl groups. We report various synthetic approaches that can lead to the synthesis of all the 64 stereoisomers of the bis-THF rings enroute to a library of Annonaceous acetogenins. The four key reactions: Sharpless asymmetric epoxidation and dihydroxylation, rhenium(VII) oxide-mediated oxidative cyclization and Shi reaction, outline the development of the bi-directional approach.  |
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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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