Studies on the Synthesis of the Alkaloid (−)-Gilbertine via Indolidene Chemistry

A synthesis route to the pentacyclic alkaloid (−)-gilbertine, which features a cyclization cascade passing through a transient indolidene intermediate, was pursued. A key stereochemical relationship was set via a Nicholas-type enolate alkylation. Ultimately, undesired C–N cyclization thwarted the fi...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-06, Vol.81 (11), p.4566-4575
Main Authors: Feldman, Ken S, Folda, Tamara S
Format: Article
Language:English
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Summary:A synthesis route to the pentacyclic alkaloid (−)-gilbertine, which features a cyclization cascade passing through a transient indolidene intermediate, was pursued. A key stereochemical relationship was set via a Nicholas-type enolate alkylation. Ultimately, undesired C–N cyclization thwarted the final projected C–C bond forming ring closure, and gilbertine could not be prepared by this route.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00348