Brief diels alder syntheses of (±)-methyl 5-epishikimate and (±)-methyl CIS-3, 4-dihydro-3, 4-dihydroxybenzoate.

MM Campbell, AD Kaye, M Sainsbury

Index: Campbell, Malcolm M.; Kaye, Aston D.; Sainsbury, Malcolm Tetrahedron Letters, 1983 , vol. 24, # 43 p. 4745 - 4746

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Citation Number: 22

Abstract

Abstract Base-catalysed ring opening of the acetonide of cis-exo-2, 3-dihydroxy-6- methoxycarbonyl-7-oxabicycloheptane affords a stereo-controlled routeto (±)-methyl 5- epishikimate and thence, by an elimination process, to (±)-methyl-cis-3, 4-dihydro-3, 4- dihydroxybenzoate.