Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 11, Pages 4566-4575Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00348
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- Chemical Synthesis Division of the National Science Foundation [CHE1361260]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1361260] Funding Source: National Science Foundation
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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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