Tetrahedron Asymmetry p. 1935 - 1944 (1994)
Update date:2022-07-30
Topics:
Katoh, Osamu
Sugai, Takeshi
Ohta, Hiromichi
Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70percent yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87percent e.e.), to be the starting material for the synthesis of optically active natural products.Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation.Final products were enantiomerically enriched to 94-95percent e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.
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Doi:10.1021/jo00120a029
(1995)Doi:10.1039/P19940002603
(1994)Doi:10.1016/j.ejmech.2014.03.010
(2014)Doi:10.1007/s11426-015-5382-1
(2015)Doi:10.1021/jo00100a049
(1994)Doi:10.1016/S0040-4020(01)89277-2
(1994)