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

doi:10.1055/s-1998-1805

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

Abstract

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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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