ORGN 37 |
| The marine alkaloid lepadiformine (1), isolated in 1994 from the ascidian Clavelina lepadiformis, was found to be moderately cytotoxic against various tumor cell lines in vitro. A model study has been examined towards the asymmetric synthesis of lepadiformine. A novel N-acylpyridinium salt reaction has been performed on 4-methoxy-5,6,7,8-tetrahydroquinoline to yield compound 5. The key steps in our proposed synthesis are a stereoselective alkylation of the dimethyl phenylsilane derivative of compound 4 followed by a stereoselective dihydroxylation/ epoxidation formation on 3. Lepadiformine will arise from the boc-carbamate cleavage followed by 5-membered ring cyclization of compound 2. Our recent progress en route to an enantioselective total synthesis of (-)-lepadiformine will be presented.
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Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- 202B, Oral
Division of Organic Chemistry |
