title: Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A.
abstract: The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described.
authors.affiliation: Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
authors.forename: Gregory L
authors.initials: GL
authors.lastname: Adams
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C528219:scholarisine A