Assembly intermediates in polyketide biosynthesis; enantioselective syntheses of beta-hydroxycarbonyl compounds

Christine Le Sann, C.L. Willis, T.J. Simpson, P. Watts, D.M. Munoz, N. Saunders, D.I. Smith, F. Soulas

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A versatile approach for the enantioselective synthesis of functionalised beta-hydroxy N-acetylcysteamine thiol esters has been developed which allows the facile incorporation of isotopic labels. It has been shown that a remarkable reversal of selectivity occurs in the titanium mediated aldol reaction of the acyloxazolidone intermediate using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted gamma-lactones.
Original languageEnglish
Pages (from-to)1719-1728
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume3 (9)
Issue number9
DOIs
Publication statusPublished - 07 Jan 2005

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

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    Le Sann, C., Willis, C. L., Simpson, T. J., Watts, P., Munoz, D. M., Saunders, N., Smith, D. I., & Soulas, F. (2005). Assembly intermediates in polyketide biosynthesis; enantioselective syntheses of beta-hydroxycarbonyl compounds. Organic and Biomolecular Chemistry, 3 (9)(9), 1719-1728. https://doi.org/10.1039/b419492f