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

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

Research output: Contribution to journalArticle

18 Citations (Scopus)

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

Fingerprint

Secologanin Tryptamine Alkaloids
Alkaloids
Monoterpenes
Cycloaddition
Lactones
Esters
alstilobanine A

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Feng, Yiqing ; Majireck, Max M. ; Weinreb, Steven M. / Total synthesis of the unusual monoterpenoid indole alkaloid (±)-alstilobanine A. In: Angewandte Chemie - International Edition. 2012 ; Vol. 51, No. 51. pp. 12846-12849.
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Total synthesis of the unusual monoterpenoid indole alkaloid (±)-alstilobanine A. / Feng, Yiqing; Majireck, Max M.; Weinreb, Steven M.

In: Angewandte Chemie - International Edition, Vol. 51, No. 51, 14.12.2012, p. 12846-12849.

Research output: Contribution to journalArticle

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