Synthesis of (-)-methyl shikimate via enzymatic resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one.
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.
Oritani
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T
Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Ueda
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R
Kiyota
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H
D001671:Biochemistry / Q000379:methods*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D012765:Shikimic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism
C453474:4-hydroxy-6-oxabicyclo(3.2.1)oct-2-en-7-one; D019086:Bridged Bicyclo Compounds, Heterocyclic; C453473:methyl shikimate; D012765:Shikimic Acid; D008049:Lipase