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

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초록

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.

키워드

BIOMIMETIC ALKALOID SYNTHESESASPIDOSPERMA ALKALOIDSALLYLIC OXIDATIONPRIMARY ALCOHOLSINDOLE SYNTHESIS(+/-)-ASPIDOSPERMIDINE(-)-ASPIDOSPERMIDINE(-)-VINCADIFFORMINE(+/-)-TABERSONINEREARRANGEMENT
제목
Directed Fischer Indolization as an Approach to the Total Syntheses of (+)-Aspidospermidine and (-)-Tabersonine
저자
Kim, Joo-YoungSuhl, Chang-HeonLee, Joon-HoCho, Cheon-Gyu
DOI
10.1021/acs.orglett.7b03078
발행일
2017-11
유형
Article
저널명
Organic Letters
19
22
페이지
6168 ~ 6171