title: Conjugate addition-dipolar cycloaddition cascade for the synthesis of benzo[a]quinolizine and indolo[a]quinolizine scaffolds: application to the total synthesis of (+/-)-yohimbenone.
abstract: A highly efficient total synthesis of (+/-)-yohimbenone and a formal synthesis of (+/-)-emetine is described. The key element of the synthesis consists of a conjugate addition-dipolar cycloaddition of 2,3-bis(phenylsulfonyl)-1,3-butadiene with an appropriate oxime. The resulting cycloadducts are cleaved reductively to provide azapolycyclic scaffolds with strategically placed functionality for further manipulation to the target compounds.
authors.affiliation: Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
authors.forename: Chad J
authors.initials: CJ
authors.lastname: Stearman
authors.forename: Michael
authors.initials: M
authors.lastname: Wilson
authors.forename: Albert
authors.initials: A
authors.lastname: Padwa