Conjugate Addition−Dipolar Cycloaddition Cascade for the Synthesis of Benzo[a]quinolizine and Indolo[a]quinolizine Scaffolds: Application to the Total Synthesis of (±)-Yohimbenone

Authors

Chad J. Stearman, Missouri State UniversityFollow
Michael Wilson
Albert Padwa

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.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

https://doi.org/10.1021/jo9003579

Keywords

mixtures, organic synthesis, organic compounds, cyclization, chemical synthesis

Publication Date

2009

Recommended Citation

Stearman, Chad J., Michael Wilson, and Albert Padwa. "Conjugate Addition− Dipolar Cycloaddition Cascade for the Synthesis of Benzo [a] quinolizine and Indolo [a] quinolizine Scaffolds: Application to the Total Synthesis of (±)-Yohimbenone." The Journal of organic chemistry 74, no. 9 (2009): 3491-3499.

Journal Title

The Journal of organic chemistry