Preparation of intermediates for the synthesis of polycyclic alkaloids: A new access to the azabicyclic core of the Stemona alkaloids

Pau Cid, Montserrat Closa, Pedro De March, Marta Figueredo, Josep Font, Elena Sanfeliu, Angeles Soria

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

Abstract

Several isoxazolidines, derived from the 1,3-dipolar cycloaddition of α,β-hexenolides to cyclic nitrones, were converted into the corresponding piperidine- and pyrrolidine-oxepinones by reduction of the nitrogen-oxygen bond. The potential of the resulting amino alcohols as synthetic precursors of polycyclic alkaloids was explored. These intermediates provide a new access to the 1-azabicyclo[5.3.0]decane core of the Sfemona alkaloids. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Original languageEnglish
Pages (from-to)4215-4233
JournalEuropean Journal of Organic Chemistry
Issue number20
DOIs
Publication statusPublished - 11 Oct 2004

Keywords

  • Isoxazolidine
  • Oxepinone
  • Piperidine
  • Polycyclic alkaloids
  • Pyrrolidine
  • Stemona

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