ORGN 479 |
Chemoenzymatic enantioselective synthesis of Imperanene
| Kirpal S. Bisht, Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, FL 33620 and Jason A. Carr, Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, SCA 400, Tampa, FL 33620. |
| Imperanene (2), a phenolic compound of the rare C6-C4-C6 class of natural products, has been shown to possess platelet aggregation inhibitory activity. Presented herein is the synthesis of imperanene (2) from vanillin (1) in nine steps in high yield and high enantioselectivity (> 97% ee). The key step in the synthesis utilizes the use of lipases, namely Pseudomonas cepacia (PS-30), via enzymatic desymmetrization of a prochiral 1,3-diol.  |
| |
|
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
|