A stereoselective cyclisation cascade mediated by SmI2-H 2O: Synthetic studies towards stolonidiol

Thomas M. Baker, Lisa A. Sloan, Lokman H. Choudhury, Masahito Murai, David J. Procter

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemoselective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol.

Original languageEnglish
Pages (from-to)1246-1261
Number of pages16
JournalTetrahedron Asymmetry
Volume21
Issue number9-10
DOIs
Publication statusPublished - May 17 2010

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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