A new and efficient chemoenzymatic route to both enantiomers of a-acetoxy and a-hydroxy-a-methoxy cyclic enones

Demir, ASCaliskan, ZAydin, AEBicer, I2024-09-182024-09-1820060957-4166https://doi.org/10.1016/j.tetasy.2006.01.025https://hdl.handle.net/20.500.12483/13287A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP afforded (+)-4b and (-)-3b in high enantiomeric excesses (91-94%) and good chemical yields. (c) 2006 Elsevier Ltd All rights reserved.eninfo:eu-repo/semantics/closedAccessManganese(Iii) AcetateStereoselective SynthesisAsymmetric-SynthesisOxidationCombinationDerivativesAcyloxyKetonesDiosphenolsAcidA new and efficient chemoenzymatic route to both enantiomers of a-acetoxy and a-hydroxy-a-methoxy cyclic enonesArticle17578679110.1016/j.tetasy.2006.01.0252-s2.0-33645833444N/AWOS:000236986100010Q2