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

Ken S. Feldman; Tamara S. Folda

doi:10.1021/acs.joc.6b00348

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

Ken S. Feldman, Tamara S. Folda

Chemistry

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4566-4575
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	81
Issue number	11
DOIs	https://doi.org/10.1021/acs.joc.6b00348
State	Published - Jun 3 2016

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/acs.joc.6b00348

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abstract = "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.",

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AB - 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.

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

Abstract

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