4 years ago

Directed Fischer Indolization as an Approach to the Total Syntheses of (+)-Aspidospermidine and (−)-Tabersonine

Directed Fischer Indolization as an Approach to the Total Syntheses of (+)-Aspidospermidine and (−)-Tabersonine
Chang-Heon Suhl, Joo-Young Kim, Cheon-Gyu Cho, Joon-Ho Lee
A conceptually new synthetic approach that provides general access to the aspidosperma alkaloids (+)-aspidospermidine and (−)-tabersonine was developed. This method is based on the regioselective indolization of an ene–hydrazide, which was obtained via a base-catalyzed intramolecular aza-Michael reaction, in situ trapping of the resulting enolate, and subsequent C–N coupling with phenyl hydrazide.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03078

DOI: 10.1021/acs.orglett.7b03078

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