159690-59-2Relevant academic research and scientific papers
Application of Microbial Enantiofacially Selective Hydrolysis in Natural Product Synthesis
Katoh, Osamu,Sugai, Takeshi,Ohta, Hiromichi
, p. 1935 - 1944 (1994)
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.
