19778-10-0Relevant academic research and scientific papers
Conjugate addition - Dipolar cycloaddition cascade for the synthesis of benzo[a]quinolizine and indolo[a]quinolizine scaffolds: Application to the total synthesis of (±)-yohimbenone
Stearman, Chad J.,Wilson, Michael,Padwa, Albert
experimental part, p. 3491 - 3499 (2009/09/08)
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)-l,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.
