Chemo‐Enzymatic Approach to Statin Side‐Chain Building Blocks
Authors:
- 3 June 2003
- journal article
- update
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 345 (6-7) , 713-715
Abstract
A versatile statin side‐chain building block is obtained by an enzymatic desymmetrisation of the symmetrical glutaric acid diethyl ester. The monoacid is produced in almost quantitative yield in the desired high optical purity. The monoacid is easily converted to the corresponding acid chloride, which is a key compound to be elaborated to some statin side‐chain derivatives. The optically active C‐5 chain is subsequently elongated by two carbon atoms and syn‐reduced to the final diol fragment.Keywords
This publication has 9 references indexed in Scilit:
- Synthesis of optically pure ethyl ( S )-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genesApplied Microbiology and Biotechnology, 2001
- Enzymatic Acylation and Ring-Closing Olefin Metathesis: A Convenient Strategy for the Lactone Moiety of Compactin and MevinolinThe Journal of Organic Chemistry, 2000
- Asymmetric synthesis of 3,5-dihydroxy-6(E)-heptenoate-containing HMG-CoA reductase inhibitorsTetrahedron, 1997
- Practical Large Scale Synthesis of tert-Butyl (3R,5S)-6-Hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate: Essential Building Block for HMG-CoA Reductase InhibitorsSynthesis, 1995
- Enantioselective microbial reduction of 3,5-dioxo-6-(benzyloxy) hexanoic acid, ethyl esterEnzyme and Microbial Technology, 1993
- Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diolsThe Journal of Organic Chemistry, 1993
- Recent advances in the staudinger reactionTetrahedron, 1992
- HMG‐CoA Reductase Inhibitors: An Exciting Development in the Treatment of HyperlipoproteinemiaMedicinal Research Reviews, 1991
- Chemoenzymatic synthesis of A C5-chiral building block: A substrate modification approach.Tetrahedron Letters, 1987