ORGN 853 |
| Acutumine was isolated from the plant Menispermum dauricum DC in 1929, and its unprecedented chlorine-containing, tetracyclic alkaloid structure, including absolute stereochemistry, was elucidated in 1967 through the application of chemical degradation and X-ray crystallographic methods. In addition to its intriguing architecture, acutumine has also shown promising varied biological activity. It was shown in 2002 that acutumine is a moderately selective inhibitor (IC50 = 13.2 ƒÝM) of human T cell growth in vivo, and animal experimental models revealed in 2003 the memory enhancing properties of acutumine. Our current approach toward a synthesis of acutumine and related structures seeks to rely on classical carbonyl reactivity to rapidly and efficiently access the acutumine architecture from the parent pyrrolidine ring. |
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Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 134, Oral
Division of Organic Chemistry |