ORGN 429 |
| Justin K. Belardi, Heidi L. Shimp, Lindsay Curtis, Steven S. Clareen, and Eduard Casillas. Department of Chemistry, Villanova University, 800 E. Lancaster Ave., Villanova, PA 19085 |
| The phytotoxin, helminthosporol, produced by the pathogenic fungus, Helminthosporum sativum, possesses moderate inhibitory activity against Acyl-CoA cholesterol acyltransferase (ACAT). The focus of the project is to synthesize helminthosporol and several analogs in order to determine structure/activity relationships. A synthetic strategy centering on the divinylcyclopropane rearrangement of a [3.1.0]-bicyclooctanone has been favorable for one analog prepared from 4,5-dimethylcyclopentenone. For helminthosporol itself, the preparation of the corresponding hydroxymethyl-cyclopentenone has been successful using a silyl-directed Nazarov cyclization. Noteworthy is the utility of the Nazarov even in the presence an allylic ester. The presentation will detail the Nazarov strategy and the synthetic progress towards the natural product and its analogs. |
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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 |