Synthesis of (−)-Methyl Shikimate via Enzymatic Resolution of (1S^*, 4R^*, 5R^*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

抄録

The synthesis of methyl (−)-shikimate [(−)-2] was achieved via lipase-catalyzed optical resolution of (1S^*,4R^*,5R^*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (−)-3. This compound was converted to (−)-2 in two steps.