ORGN 424 |
Synthetic efforts toward (-)-crinipellin A
| Yanping Chen, Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794-3400 and Scott McN. Sieburth, Department of Chemistry, Temple University, 1901 N. 13th street, Philadelphia, PA 19122. |
| Crinipellis stipitaria (Agarricales) is a fungus that grows on both the dead and living parts of grasses. It produces an antibacterial metabolite that was isolated and named crinipellin. The crinipellin antibiotics are active against gram-positive bacteria, yeasts, filamentous fungi, and Ehrich carcinoma ascites cells. In 1985, Steglich and coworkers determined the structures of crinipellins, which constitutes the only known tetraquinane natural products. As part of our ongoing interest in synthetic application of 2-pyridone cycloaddition reactions, we are studying the synthesis of (-)-crinipellin A by an intramolecular [4+4]-photocycloaddition of a pyridone and a furan followed by transannular ring closure.  |
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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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