Conjugate addition-dipolar cycloaddition cascade for the synthesis of benzo[a]quinolizine and indolo[a]quinolizine scaffolds: application to the total synthesis of (+/-)-yohimbenone.
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.
Stearman
Chad J
CJ
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Wilson
Michael
M
Padwa
Albert
A