Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 21, Pages 8359-8368Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901986v
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Funding
- Ministerio de Ciencia c Innovacion, Spain [CTQ2006-00500/BQU]
- University of Barcelona
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An indole-templated ring-closing metathesis or it 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid apparicine From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents.
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