ORGN 744 |
| Acutumine was isolated from the plant Menispermum dauricum DC in 1929, and its unprecedented chlorine-containing, tetracyclic alkaloid structure (including its absolute stereochemistry) was elucidated in 1967 through the application of chemical degradation and X-ray crystallographic methods. In addition to its unique architecture, acutumine has also shown various promising biological activities including: in vivo inhibition of human T cell growth and memory-enhancing properties on animal models. Starting from the parent pyrrolidine ring of acutumine, a rapid and efficient synthesis is proposed to access the framework of this complex natural molecule. Our strategy mainly relies on three classical reactions: elimination/Michael addition cascade, Wagner-Meerwein rearrangement and Dieckmann condensation. Exceptional behaviors of carbonyl groups, which have been observed in the course of our work, will also be briefly highlighted.
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Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |
