SYNTHESIS OF ROCHE LACTONE VIA THE ENANTIOSELECTIVE ALCOHOLYSIS OF meso-CYCLIC ANHYDRIDE STRATEGY: A PRACTICAL APPROACH EMPLOYING AN EFFICIENT AND REUSABLE ORGANIC MICROGEL AUXILIARIES

被引:5
作者
Xiong, Fei [1 ]
Xi, Chang-Cheng [1 ]
Ma, Chao [1 ]
Chen, Lu [1 ]
Sun, Ming-Wei [1 ]
Zhang, Xing-Guang [1 ]
Hong, Dan-Feng [1 ]
机构
[1] Univ Shanghai Sci & Technol, Dept Chem, Shanghai 200093, Peoples R China
基金
中国国家自然科学基金;
关键词
DESYMMETRIZATION; (+)-BIOTIN;
D O I
10.3987/COM-20-14386
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Roche lactone, a key chiral intermediate of the natural water-soluble B series vitamin (+)-biotin, was synthesized from meso-cyclic anhydride in overall yield 78% through three steps, including heterogeneous asymmetric desymmetrization, chemoselective reduction and lactonization.
引用
收藏
页码:245 / 253
页数:9
相关论文
共 16 条
[1]   Organocatalytic enantioselective desymmetrisation [J].
Borissov, A. ;
Davies, T. Q. ;
Ellis, S. R. ;
Fleming, T. A. ;
Richardson, M. S. W. ;
Dixon, D. J. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (20) :5474-5540
[2]   Reversible Switching and Recycling of Adaptable Organic Microgel Catalysts (Microgelzymes) for Asymmetric Organocatalytic Desymmetrization [J].
Borrmann, Ruediger ;
Palchyk, Volodymyr ;
Pich, Andrij ;
Rueping, Magnus .
ACS CATALYSIS, 2018, 8 (09) :7991-7996
[3]   Synthetic Studies on (+)-Biotin, Part 151): A Chiral Squaramide-Mediated Enantioselective Alcoholysis Approach toward the Total Synthesis of (+)-Biotin [J].
Chen, Xu-Xiang ;
Xiong, Fei ;
Fu, Han ;
Liu, Zhi-Qian ;
Chen, Fen-Er .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (04) :488-491
[4]   Synthetic studies on (+)-biotin, Part 11:: Application of Cinchona alkaloid-mediated asymmetric alcoholysis of meso-cyclic anhydride in the total synthesis of (+)-biotin [J].
Dai, Hui-Fang ;
Chen, Wen-Xue ;
Zhao, Lei ;
Xiong, Fei ;
Sheng, Hao ;
Chen, Fen-Er .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (10) :1635-1641
[5]   Biotin: A timeless challenge for total synthesis [J].
DeClercq, PJ .
CHEMICAL REVIEWS, 1997, 97 (06) :1755-1792
[6]   Biological significance and development of practical synthesis of biotin [J].
Seki, Masahiko .
MEDICINAL RESEARCH REVIEWS, 2006, 26 (04) :434-482
[7]  
Tang Pei, 2020, PHARM FRONTS, V02, pe28
[8]  
[谢斌 XIE Bin], 2008, [中国药物化学杂志, Chinese Journal of Medicinal Chemistry], V18, P468
[9]  
Xiong F, 2018, INDIAN J HETEROCY CH, V28, P429
[10]   PREPARATION OF (+)-BIOTIN: PROCESS DEVELOPMENT AND SCALE-UP [J].
Xiong, Fei ;
Li, Jin ;
Li, Gen ;
Song, Bo ;
Zhou, Yu-Xiao ;
Chen, Fen-Er ;
Li, Dan .
HETEROCYCLES, 2016, 92 (03) :544-551