title: Total synthesis of (+)-aspidospermidine: a new strategy for the enantiospecific synthesis of aspidosperma alkaloids.
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.
authors.affiliation: Department of Chemistry, The University of Michigan, Ann Arbor 48109, USA. jpmarino@nd.edu
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Marino
authors.forename: Maria B
authors.initials: MB
authors.lastname: Rubio
authors.forename: Ganfeng
authors.initials: G
authors.lastname: Cao
authors.forename: Alfonso
authors.initials: A
authors.lastname: de Dios
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D030009:Aspidosperma / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; C409672:aspidospermidine