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 journalArticle

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
Externally publishedYes

Fingerprint

Cyclization
cascades
Bearings (structural)
Lactones
products
cyclopentanol
stolonidiol
3-hydroxybutanal

ASJC Scopus subject areas

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

Cite this

A stereoselective cyclisation cascade mediated by SmI2-H 2O : Synthetic studies towards stolonidiol. / Baker, Thomas M.; Sloan, Lisa A.; Choudhury, Lokman H.; Murai, Masahito; Procter, David J.

In: Tetrahedron Asymmetry, Vol. 21, No. 9-10, 17.05.2010, p. 1246-1261.

Research output: Contribution to journalArticle

Baker, Thomas M. ; Sloan, Lisa A. ; Choudhury, Lokman H. ; Murai, Masahito ; Procter, David J. / A stereoselective cyclisation cascade mediated by SmI2-H 2O : Synthetic studies towards stolonidiol. In: Tetrahedron Asymmetry. 2010 ; Vol. 21, No. 9-10. pp. 1246-1261.
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