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Asymmetric Heck cyclization route to indolizidine and azaazulene alkaloids: synthesis of (+)-5-epiindolizidine 167B and indolizidine 223AB

✍ Scribed by Kurt Kiewel; Mathew Tallant; Gary A Sulikowski

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 85 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01361-2

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✦ Synopsis

Asymmetric intramolecular Heck cyclization of endocyclic enamides occurs at room temperature to give indoloizidine and azaazulene ring systems in up to 86% enantiomeric excess. A synthesis of (+)-epiindolizidine 167B and formal synthesis of 5E,9Z-indolizidine 223AB is described.

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