A new synthetic route to methyl (-)-shikimate by asymmetric diels-alder reaction of (S)s-3-(2-pyridylsulfinyl)acrylate.

Abstract

A 7-oxabicyclo[2.2.1]heptene derivative ((7a)___-) that substituted effectively for the synthesis of (-)-shikimic acid was prepared by an asymmetric Diels-Alder reaction of (S__-)S-3-(2-pyridylsulfinyl)acrylate (2__-) with 3, 4-dibenzyloxyfuran (4__-). The bicyclic compound ((7a)___-) was converted to methyl (-)-triacetylshikimate ((14)___-) (via)___- the (endo)___--(cis)___- dibenzyloxy derivative ((11)___-).