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Synlett 1998; 1998(8): 828-830
DOI: 10.1055/s-1998-1805
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Synthesis of β-ketophosphonates from Thioester Intermediates: A Stereocontrolled Route to the C29,C35 Fragment of the Halichondramides

Alison N. Hulme* , Garnet E. Howells, Rachel H. Walker
  • *Department of Chemistry, The University of Edinburgh, King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK; E-mail: Alison.Hulme@ed.ac.uk
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Publication Date:
31 December 2000 (online)

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An efficient synthesis of β-ketophosphonates from t-butyl thioesters using the lithium anion of either methane- or ethanephosphonate is described. The elaboration of a range of substrates to intermediates in natural product syntheses via the Horner Wadsworth Emmons reaction is then discussed.

thioesters - anti-aldol - β-ketophosphonate - Horner Wadsworth - Emmons reaction

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