Synthesis of Functionalized 2,3- and 3,4-Dihydropyrans Starting from α-Hydroxycarboxylic Esters via RCM

Bernd Schmidt; Holger Wildemann

doi:10.1055/s-1999-2884

Synlett 1999; 1999(10): 1591-1593
DOI: 10.1055/s-1999-2884

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Synthesis of Functionalized 2,3- and 3,4-Dihydropyrans Starting from α-Hydroxycarboxylic Esters via RCM

Bernd Schmidt^* , Holger Wildemann

^*Universität Dortmund, Fachbereich Chemie, Organische Chemie I, D-44221 Dortmund, Germany; Fax + 49(2 31)7 55 53 63; E-mail: bschmidt@citrin.chemie.uni-dortmund.de

Abstract

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α-Hydroxy carboxylic acids and their derivatives are naturally occurring starting materials for the synthesis of functionalized tetrahydropyrans using ring closing metathesis and base induced epoxide rearrangement as key steps. (S)-Lactic acid methyl ester has been used as the starting material for the preparation of enantiomerically pure 6-desoxy C-glycoside precursors.

metathesis - pyrans - glycals - epoxidation

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