Abstract
Reaction of (−)-methyl shikimate ((−) with 2-acetoxyisobutyryl bromide afforded (+)-methyl (3R,4S,5R)-3-bromo-4-acetoxy-5-hydroxy-1-cyclohexene-1-carboxylate ((+). Transesterification of this bromoacetate with NaOCH 3 led quantitatively to the corresponding epoxyol, (+)-methyl 3,4-anhydroshikimate. Payne rearrangement of this trans-epoxyol produced (−)-methyl (3S,4S,5R)-3-hydroxy-4,5-epoxy-1-cyclohexene-1-carboxylate ((−), which has previously been converted into (−)-chorismic acid
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