Premium
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