title: Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline.
abstract: A novel approach to the tricyclic core of the Stemona alkaloids stemofoline and didehydrostemofoline has been discovered that features an intramolecular (3+2) dipolar cycloaddition of an unactivated carbon-carbon double bond with an azomethine ylide; the azomethine ylide was generated by an unprecedented reaction that occurred during a Swern oxidation of an α-(N-cyanomethyl)-β-hydroxy ester. In separate experiments, the efficacy of introducing the requisite oxygen functionality at C(8) and the 1-butenyl side chain at C(3) was established.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas, Austin, TX USA 78712.
authors.forename: Jochen
authors.initials: J
authors.lastname: Dietz
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin