Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Esters with Biscarbamate Protection and Its Application to the Synthesis of xCT Inhibitors

被引:5
作者
Yasuno, Yoko [1 ]
Mizutani, Iho [1 ]
Sueuchi, Yuki [1 ]
Wakabayashi, Yuuka [1 ]
Yasuo, Nozomi [1 ]
Shimamoto, Keiko [2 ]
Shinada, Tetsuro [1 ]
机构
[1] Osaka City Univ, Grad Sch Sci, Sumiyoshi Ku, Osaka 5588585, Japan
[2] Suntory Fdn Life Sci, Bioorgan Res Inst, 8-1-1 Seikadai,Seika Cho, Kyoto 6190284, Japan
关键词
asymmetric catalysis; cystine-glutamate exchanger; dehydroamino acids; diaminosuberic acids; hydrogenation; orthogonal protection; ANTIPORTER SYSTEM X(C)(-); ALPHA-AMINO ACIDS; STEREOSELECTIVE-SYNTHESIS; DIAMINOSUBERIC ACID; EFFICIENT SYNTHESIS; ONE-POT; CYSTINE/GLUTAMATE ANTIPORTER; 2,7-DIAMINOSUBERIC ACID; DERIVATIVES; TRANSPORT;
D O I
10.1002/chem.201900289
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic asymmetric hydrogenation of dehydroamino acid esters with biscarbamate protection was examined for the first time to prepare optically active amino acids. The new method was successfully applied to the synthesis of new cystine-glutamate exchanger inhibitors.
引用
收藏
页码:5145 / 5148
页数:4
相关论文
共 54 条
[1]   Synthesis of diaminosuberic acid derivatives via ring-closing alkyne metathesis [J].
Aguilera, B ;
Wolf, LB ;
Nieczypor, P ;
Rutjes, FPJT ;
Overkleeft, HS ;
van Hest, JCM ;
Schoemaker, HE ;
Wang, B ;
Mol, JC ;
Fürstner, A ;
Overhand, M ;
van der Marel, GA ;
van Boom, JH .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3584-3589
[2]   PREPARATION OF HORNER-WADSWORTH-EMMONS REAGENT: METHYL 2-BENZYLOXYCARBONYLAMINO-2-(DIMETHOXY-PHOSPHINYL)ACETATE [J].
Azuma, Hiroki ;
Okano, Kentaro ;
Fukuyama, Tohru ;
Tokuyama, Hidetoshi .
ORGANIC SYNTHESES, 2011, 88 :152-+
[3]   Amino Acid Transporters in Cancer and Their Relevance to "Glutamine Addiction": Novel Targets for the Design of a New Class of Anticancer Drugs [J].
Bhutia, Yangzom D. ;
Babu, Ellappan ;
Ramachandran, Sabarish ;
Ganapathy, Vadivel .
CANCER RESEARCH, 2015, 75 (09) :1782-1788
[4]  
Blaskovich M. A., 2010, HDB SYNTHESES AMINO, P265
[5]   Thinking Outside the Cleft to Understand Synaptic Activity: Contribution of the Cystine-Glutamate Antiporter (System xc-) to Normal and Pathological Glutamatergic Signaling [J].
Bridges, Richard ;
Lutgen, Victoria ;
Lobner, Doug ;
Baker, David A. .
PHARMACOLOGICAL REVIEWS, 2012, 64 (03) :780-802
[6]   System xc- cystine/glutamate antiporter: an update on molecular pharmacology and roles within the CNS [J].
Bridges, Richard J. ;
Natale, Nicholas R. ;
Patel, Sarjubhai A. .
BRITISH JOURNAL OF PHARMACOLOGY, 2012, 165 (01) :20-34
[7]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[8]   Modular phospholane ligands in asymmetric catalysis [J].
Burk, MJ .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :363-372
[9]   One-Pot Selective Homodimerization/Hydrogenation Strategy for Sequential Dicarba Bridge Formation [J].
Burnley, James ;
Jackson, W. Roy ;
Robinson, Andrea J. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18) :9057-9063
[10]   Stereoselective synthesis of diaminosuberic acid via a chiral alkynyl oxazolidine [J].
Callahan, JF ;
Khatana, SS ;
Bhatnagar, PK .
SYNTHETIC COMMUNICATIONS, 2000, 30 (07) :1213-1219