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Synthesis 2000; 2000(10): 1409-1414
DOI: 10.1055/s-2000-7114
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De Novo Asymmetric Synthesis of Protected 5-O-Carbamoylpolyoxamic Acid

Cécile Dehoux* , Céline Monthieu, Michel Baltas, Liliane Gorrichon
  • *Laboratoire de Synthèse et Physicochimique de Molécules d'Intérêt Biologique, UMR 5068 Associée au CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 04, France; Tel. 330(5)61 55 62 93; Fax 330(5)61 55 60 11; E-mail: baltas@iris.ups-tlse.fr
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Publication Date:
31 December 2000 (online)

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The synthesis of 5-O-carbamoylpolyoxamic acid from a non carbohydrate precursor was achieved in 12 steps and 7% yield starting from chiral α,β-epoxyaldehyde readily available from cis-2-butene-1,4-diol. The main steps concern the Sharpless asymmetric epoxidation of a suitable chosen allylic alcohol, the use of thiazolyl group for carbon homologation, the stereo- and regioselective opening of the epoxide and the transformation of the primary alcohol to the acid functionality of the final product.

amino acids - antifungal agents - asymmetric synthesis - epoxide - azide