Synthesis of (−)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one
2001
ORITANI, Takayuki | UEDA, Rumi | Kiyota, Hiromasa
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.
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