Synlett 2004(2): 0350-0352  
DOI: 10.1055/s-2003-44979
LETTER
© Georg Thieme Verlag Stuttgart · New York

Furanose Synthesis via Regioselective Dihydroxylation of 1-Silyloxy-1,3-dienes: Application to the Furanose Unit of 4-epi-Hygromycin A

Alan Armstrong*a, David M. Gethinb, Christopher J. Wheelhousea
a Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK
e-Mail: A.Armstrong@imperial.ac.uk;
b Veterinary Medicine Research and Development, Pfizer Animal Health, Sandwich, Kent CT13 9NJ, UK
Further Information

Publication History

Received 7 October 2003
Publication Date:
08 December 2003 (online)

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Abstract

Asymmetric dihydroxylation of a 1-silyloxy-1,3-diene is shown to occur regioselectively on the non-oxygenated alkene. Second dihydroxylation is complicated by over-oxidation to the dione and epimerisation of reaction products. However, subsequent manipulations including selective oxidation of a primary alcohol allow synthesis of a protected furanose corresponding to that present in C4-epi-hygromycin.