Synthetic Studies on (+)‐Biotin, Part 11: Application of  Cinchona  Alkaloid‐Mediated Asymmetric Alcoholysis of  meso ‐Cyclic Anhydride in the Total Synthesis of (+)‐Biotin | Zendy

Dai HuiFang | Zendy; Chen WenXue | Zendy; Zhao Lei | Zendy; Xiong Fei | Zendy; Sheng Hao | Zendy; Chen FenEr | Zendy

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Synthetic Studies on (+)‐Biotin, Part 11: Application of Cinchona Alkaloid‐Mediated Asymmetric Alcoholysis of meso ‐Cyclic Anhydride in the Total Synthesis of (+)‐Biotin

Author(s) -

Dai HuiFang,

Chen WenXue,

Zhao Lei,

Xiong Fei,

Sheng Hao,

Chen FenEr

Publication year - 2008

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.200800151

Subject(s) - cinchona , chemistry , enantioselective synthesis , total synthesis , alkaloid , organic chemistry , biotin , palladium , combinatorial chemistry , stereochemistry , catalysis , biochemistry

A practical and asymmetric process for the total synthesis of (+)‐biotin ( 1 ) has been accomplished starting from cis ‐1,3‐dibenzyl‐2‐oxoimidazolidine‐4,5‐dicarboxylic acid ( 2 ). This approach features a highly enantioselective alcoholysis of meso ‐cyclic anhydride 3 into (4 S ,5 R )‐cinnamyl hemiester 4 mediated by Cinchona alkaloids. Another attractive feature of this synthesis involves the use of recyclable palladium nanoparticles‐catalyzed assembly of the 4‐carboxybutyl chain at C‐4 in (3 aS ,6 aR )‐thiolactone 7 employing an improved Fukuyama‐type cross‐coupling reaction

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