Chiral Holmium Complex-Catalyzed Synthesis of Hydrocarbazole from Siloxyvinylindole and Its Application to the Enantioselective Total Synthesis of (-)-Minovincine.

Abstract

The catalytic and enantioselective total synthesis of (-)-minovincine has been accomplished. The key highly substituted hydrocarbazole derivative was obtained by an asymmetric Diels-Alder reaction of siloxyvinylindole catalyzed by 0.5 mol % of a chiral holmium complex. The Diels-Alder adduct was converted to a tetracyclic intermediate in a one-pot procedure. No waste stereoisomers were produced throughout the entire total synthesis.

DOI: 10.1021/acs.joc.5b01393

Cite this paper

@article{Morikawa2015ChiralHC, title={Chiral Holmium Complex-Catalyzed Synthesis of Hydrocarbazole from Siloxyvinylindole and Its Application to the Enantioselective Total Synthesis of (-)-Minovincine.}, author={Takahiro Morikawa and Shinji Harada and Atsushi Nishida}, journal={The Journal of organic chemistry}, year={2015}, volume={80 17}, pages={8859-67} }