title: Total synthesis of (+)-scholarisine A.
abstract: An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.
authors.affiliation: Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
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: D018360:Crystallography, X-Ray; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C528219:scholarisine A