title: Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.
abstract: A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
authors.forename: Adam T
authors.initials: AT
authors.lastname: Hoye
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; C559343:sessilifoliamide C; C519217:stemoamide