A practical stereoselective synthesis of (2R,3S)-alloisoleucine

被引:31
作者
Portonovo, P [1 ]
Liang, B [1 ]
Joullié, MM [1 ]
机构
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0957-4166(99)00118-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient asymmetric Strecker synthesis of the unnatural alpha-amino acid, D-alloisoleucine (3), from commercially available and inexpensive (S)-2-methyl-1-butanol (4) was accomplished in four steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1451 / 1455
页数:5
相关论文
共 23 条
[1]  
ANELLI P, 1993, TEMPO CATALYZED OXID, P367
[2]  
AOYAGI T, 1978, BIOACTIVE PEPTIDES P, P137
[3]   A straightforward, highly stereoselective synthesis of protected isostatine derivatives [J].
Castejon, P ;
Moyano, A ;
Pericas, MA ;
Riera, A .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (08) :1001-1006
[4]  
CASTRO B, 1987, CHEM BIOL P AM PEPT, P656
[5]   1,3-DIASTEREOCONTROL WITH BROMOALLENES - SYNTHESIS OF ENANTIOMERICALLY PURE BETA-BRANCHED ALPHA-AMINO-ACIDS [J].
DANIELLO, F ;
MANN, A ;
TADDEI, M ;
WERMUTH, CG .
TETRAHEDRON LETTERS, 1994, 35 (42) :7775-7778
[6]   Asymmetric Strecker synthesis using enantiopure sulfinimines and diethylaluminum cyanide: The alcohol effect [J].
Davis, FA ;
Portonovo, PS ;
Reddy, RE ;
Chiu, YH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :440-441
[7]   ASYMMETRIC-SYNTHESIS OF SULFINIMINES - CHIRAL AMMONIA IMINE SYNTHONS [J].
DAVIS, FA ;
REDDY, RE ;
SZEWCZYK, JM ;
PORTONOVO, PS .
TETRAHEDRON LETTERS, 1993, 34 (39) :6229-6232
[8]   CONVENIENT RESOLUTION METHOD FOR PREPARATION OF ISOLEUCINE OPTICAL ISOMERS [J].
FLOURET, G ;
NAKAGAWA, SH .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (18) :2635-2637
[9]   SYNTHETIC STUDIES OF DIDEMNINS .3. SYNTHESES OF STATINE AND ISOSTATINE STEREOISOMERS [J].
HARRIS, BD ;
JOULLIE, MM .
TETRAHEDRON, 1988, 44 (12) :3489-3500
[10]   CRYSTAL AND MOLECULAR-STRUCTURE OF DIDEMNIN B, AN ANTIVIRAL AND CYTO-TOXIC DEPSIPEPTIDE [J].
HOSSAIN, MB ;
VANDERHELM, D ;
ANTEL, J ;
SHELDRICK, GM ;
SANDUJA, SK ;
WEINHEIMER, AJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (12) :4118-4122