An efficient asymmetric synthesis of (2S,3S)- and (2R,3R)-β-hydroxyornithine

被引:13
作者
DeMong, DE [1 ]
Williams, RM [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)01945-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric syntheses of (2S,3S)- and (2R,3R)-beta -hydroxyornithine have been achieved in four steps and 46% overall yield. The key step in this synthesis involved an aldol reaction between a chiral glycine boron enolate and (3-oxo-propyl)-carbamic acid benzyl ester. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:183 / 185
页数:3
相关论文
共 15 条
[1]   STUDIES ON THE BIOSYNTHESIS OF CLAVULANIC ACID .4. SYNTHETIC ROUTES TO THE MONOCYCLIC BETA-LACTAM PRECURSOR, PROCLAVAMINIC ACID [J].
BAGGALEY, KH ;
ELSON, SW ;
NICHOLSON, NH ;
SIME, JT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1513-1520
[2]   ISOLATION OF AN INTERMEDIATE IN CLAVULANIC ACID BIOSYNTHESIS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BRYANS, JS ;
BRINGHEN, AO ;
COATES, JB ;
CROUCH, NP ;
LLOYD, MD ;
SCHOFIELD, CJ ;
ELSON, SW ;
BAGGALEY, KH ;
CASSELLS, R ;
NICHOLSON, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (08) :617-619
[3]   A STEREOSELECTIVE SYNTHESIS OF 3(R)-HYDROXY-2(S)-ORNITHINE [J].
DIGIOVANNI, MC ;
MISITI, D ;
ZAPPIA, G ;
DELLEMONACHE, G .
TETRAHEDRON, 1993, 49 (48) :11321-11328
[4]   ISOLATION OF 2 NOVEL INTRACELLULAR BETA-LACTAMS AND A NOVEL DIOXYGENASE CYCLIZING ENZYME FROM STREPTOMYCES-CLAVULIGERUS [J].
ELSON, SW ;
BAGGALEY, KH ;
GILLETT, J ;
HOLLAND, S ;
NICHOLSON, NH ;
SIME, JT ;
WORONIECKI, SR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (22) :1736-1738
[5]   BIOSYNTHESIS OF ACIVICIN .3. INCORPORATION OF ORNITHINE AND N(DELTA)-HYDROXYORNITHINE [J].
GOULD, SJ ;
JU, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10166-10172
[6]  
HASHIDOKO Y, 1998, TENNEN YUKI KAGOBUTS, V40, P455
[7]   STEREOCHEMICAL CORRELATION OF PROCLAVAMINIC ACID AND SYNTHESES OF ERYTHRO-L-BETA-HYDROXYORNITHINE AND THREO-L-BETA-HYDROXYORNITHINE FROM AN IMPROVED VINYLGLYCINE SYNTHON [J].
KROL, WJ ;
MAO, SS ;
STEELE, DL ;
TOWNSEND, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :728-731
[8]   Stereoselective synthesis of [2S,3R]-beta-hydroxy ornithine [J].
Rao, BV ;
Krishna, UM ;
Gurjar, MK .
SYNTHETIC COMMUNICATIONS, 1997, 27 (08) :1335-1345
[9]   ASYMMETRIC ALDOL REACTIONS USING BORON ENOLATES OF CHIRAL OXAZINONES, SYNTHESIS OF L-ALLO-THREONINE [J].
RENO, DS ;
LOTZ, BT ;
MILLER, MJ .
TETRAHEDRON LETTERS, 1990, 31 (06) :827-830
[10]   Synthetic studies on tetrazomine:: Stereochemical assignment of the β-hydroxypipecolic acid [J].
Scott, JD ;
Tippie, TN ;
Williams, RM .
TETRAHEDRON LETTERS, 1998, 39 (22) :3659-3662