Efficient synthesis of (-)-methyl 3-epi-shikimate and methyl 3-eqi-quinate by one-pot selective protection of trans-1,2-diols

trans-1,2-Diol protections of shikimic and quinic acids have been achieved by in situ formation of the protecting group (2,2,3,3-tetramethoxybutane). The synthetic utility of the protected derivatives is demonstrated by the preparation of (-)-methyl 3-epi-shikimate and methyl 3-epi-quinate through a new and efficient route from the parent acids. (C) 2000 Published by Elsevier Science Ltd.