Total synthesis of the unusual monoterpenoid indole alkaloid (±)-alstilobanine A

Yiqing Feng, Max M. Majireck, Steven M. Weinreb

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

Tetracyclic monoterpene alkaloid alstilobanine A was obtained in racemic form. The pivotal steps of the total synthesis are a novel conjugate addition of an ester enolate with a nitrosoalkene, as well as a formal [2+2] intramolecular cycloaddition leading to a β-lactone to generate the requisite cis-fused 2-azadecalin moiety of the alkaloid. TMSE=trimethylsilylethoxy, Ts=4-toluenesulfonyl.

Original languageEnglish (US)
Pages (from-to)12846-12849
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number51
DOIs
StatePublished - Dec 14 2012

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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