Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids

Ramon Alibés, Pilar Blanco, Eva Casas, Montserrat Closa, Pedro De March, Marta Figueredo, Josep Font, Elena Sanfeliu, Ángel Álvarez-Larena

Research output: Contribution to journalArticleResearchpeer-review

32 Citations (Scopus)

Abstract

(Chemical Equation Presented) A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C6 olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids. © 2005 American Chemical Society.
Original languageEnglish
Pages (from-to)3157-3167
JournalJournal of Organic Chemistry
Volume70
Issue number8
DOIs
Publication statusPublished - 15 Apr 2005

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