A new and efficient chemoenzymatic route to both enantiomers of 4-hydroxycyclohex-2-en-1-one.
[reaction: see text] A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-hydroxycyclohex-2-en-1-one in three steps starting from 3-methoxycyclohex-2-en-1-one is described. Manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of 4-hydroxycyclohex-2-en-1-one in high enantiomeric excess.
Demir
Ayhan S
AS
Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey. asdemir@metu.edu.tr
Sesenoglu
Ozge
O