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Highly Enantioselective Methanolysis of Meso ‐Cyclic Anhydride Mediated by Bifunctional Thiourea Cinchona Alkaloid Derivatives: Access to Asymmetric Total Synthesis of (+)‐Biotin
Author(s) -
Xiong Fei,
Xiong FangJun,
Chen WenXue,
Jia HuiQing,
Chen FenEr
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1512
Subject(s) - chemistry , cinchona , total synthesis , bifunctional , enantioselective synthesis , thiourea , thiolactone , organic chemistry , lactone , alkaloid , desymmetrization , stereochemistry , catalysis
An enantioselective asymmetric total synthesis of (+)−biotin ( 1 ) via the Hoffmann–Roche lactone–thiolactone strategy has been accomplished from commercially available cis ‐1,3‐dibenzyl‐2‐imidazolidone‐4,5‐dicarboxylic acid ( 2 ). Strategic transformations include a cinchona alkaloid‐based bifunctional thiourea mediated methanolytic desymmetrization of prochiral cyclic anhydride 3 to produce the enantiomerically enriched precursor of Roche lactone 5 and an improved introduction of the 4‐carboxybutyl side chain at C‐4 position of Roche thiolactone 6 via Grignard reaction .