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Synlett 1997; 1997(5): 629-631
DOI: 10.1055/s-1997-3220
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Stereoselective Synthesis of 2-(1-Alkoxyalkyl)-3-hydroxy-5-substituted-tetrahydrofurans

Gregory W. Bradley, Eric J. Thomas*
  • *Department of Chemistry, University of Manchester, Manchester M13 9PL, U.K., Fax (0)161 275 4939; e.j.thomas@man.ac.uk
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Publication Date:
31 December 2000 (online)

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Oxidation of toluene-p-sulfonates derived from 1-substituted-1,5-syn-5-benzyloxyhex-3-enols using osmium tetraoxide gives stereoselective access to 2-(1-alkoxyalkyl)-3-hydroxy-5-substituted-tetrahydrofurans. This procedure has been applied to synthesize bis-tetrahydrofurans.

allylstannane - osmylation - tetrahydrofuran - stereoselective - synthesis