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Total synthesis of (+)-aspidospermidine: a new strategy for the enantiospecific synthesis of aspidosperma alkaloids
Authors:Marino Joseph P  Rubio Maria B  Cao Ganfeng  de Dios Alfonso
Institution:Department of Chemistry, The University of Michigan, Ann Arbor 48109, USA. jpmarino@nd.edu
Abstract:A new strategy was developed for the enantiospecific synthesis of aspidosperma alkaloids. The key steps involve a novel ketene-lactonization reaction of a chiral vinyl sulfoxide to efficiently set up the quaternary carbon center, and a tandem Michael addition-alkylation reaction sequence to form the polycyclic core structure. This new strategy was employed in the total synthesis of natural product (+)-aspidospermidine.
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