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Synthetic Studies on d ‐Biotin, Part 8: [1] An Efficient Chemoenzymatic Approach to the Asymmetric Total Synthesis of d ‐Biotin via a Polymer‐Supported PLE‐Mediated Desymmetrization of meso ‐Symmetic Dicarboxylic Esters
Author(s) -
Chen FenEr,
Chen XuXiang,
Dai HuiFang,
Kuang YunYan,
Xie Bin,
Zhao JianFeng
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404311
Subject(s) - chemistry , desymmetrization , dicarboxylic acid , enantioselective synthesis , biotin , hydrolysis , esterase , total synthesis , organic chemistry , polymer , asymmetric hydrogenation , enzyme , catalysis , biochemistry
A practical chemoenzymatic method for the asymmetric total synthesis of d ‐biotin ( 1 ) starting from the commercially available cis‐ 1,3‐dibenzyl‐2‐imidazolidone‐4,5‐dicarboxylic acid ( 2 ) has been developed. The key step of the synthesis is the highly enantioselective hydrolysis of meso ‐dicarboxylic esters by a polymer‐supported pig liver esterase and introduction of a formyl group at the C‐4 position in 4 via a Grignard reaction. The polymer‐supported PLE can be recovered quantitatively from the reaction mixture by simple filtration and reused without significant loss of activity.