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

Ken S. Feldman, Tamara S. Folda

Research output: Contribution to journalArticlepeer-review

9 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 languageEnglish (US)
Pages (from-to)4566-4575
Number of pages10
JournalJournal of Organic Chemistry
Volume81
Issue number11
DOIs
StatePublished - Jun 3 2016

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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