Polyhydroxy amino acid derivatives via β-lactams using enantiospecific approaches and microwave techniques

被引:82
作者
Bose, AK [1 ]
Banik, BK [1 ]
Mathur, C [1 ]
Wagle, DR [1 ]
Manhas, MS [1 ]
机构
[1] Stevens Inst Technol, Dept Chem & Chem Technol, George Barasch Biorgan Res Lab, Hoboken, NJ 07030 USA
关键词
annulation; azetidinones; enantiospecific; amino sugars; amino acids; microwave irradiation;
D O I
10.1016/S0040-4020(00)00410-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiospecific synthesis has been developed for alpha-hydroxy beta-lactams of predictable absolute configuration starting with readily available carbohydrates, Stereospecific approaches and microwave assisted chemical reactions have been utilized for the preparation of these 3-hydroxy-2-azetidinones and their conversion to natural or non-natural enantiomeric forms of intermediates for gentosamine, 6-epilincosamine, gamma-hydroxythreonine, and polyoxamic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5603 / 5619
页数:17
相关论文
共 84 条
[1]  
ABRAMOVITCH RA, 1991, ORG PREP PROCED INT, V23, P685
[2]  
Anwar M.K., 1980, Synthesis, P929
[3]  
Baer E, 1939, J BIOL CHEM, V128, P463
[4]   An efficient synthesis of the cyclic form of scalemic 2,4-di-epi-polyoxamic acid exploiting the hetero Diels-Alder approach [J].
Bandini, E ;
Martelli, G ;
Spunta, G ;
Bongini, A ;
Panunzio, M ;
Piersanti, G .
TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3717-3718
[5]   STUDIES ON LACTAMS .96. STEREOSPECIFIC GLYCOSYLATION VIA FERRIER REARRANGEMENT FOR OPTICAL RESOLUTION [J].
BANIK, BK ;
MANHAS, MS ;
BOSE, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4714-4716
[6]   MICROWAVE-INDUCED ORGANIC-REACTION ENHANCEMENT CHEMISTRY .4. CONVENIENT SYNTHESIS OF ENANTIOPURE ALPHA-HYDROXY-BETA-LACTAMS [J].
BANIK, BK ;
MANHAS, MS ;
KALUZA, Z ;
BARAKAT, KJ ;
BOSE, AK .
TETRAHEDRON LETTERS, 1992, 33 (25) :3603-3606
[7]   Studies on lactams .99. Fused tricyclic beta-lactams via intramolecular aryl radical cyclization [J].
Banik, BK ;
Subbaraju, GV ;
Manhas, MS ;
Bose, AK .
TETRAHEDRON LETTERS, 1996, 37 (09) :1363-1366
[8]   FACILE PREPARATION OF CARBAPENEM SYNTHONS VIA MICROWAVE-INDUCED RAPID REACTION [J].
BANIK, BK ;
MANHAS, MS ;
NEWAZ, SN ;
BOSE, AK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) :2363-2368
[9]  
Banik BK, 1997, HETEROCYCLES, V44, P405
[10]   Microwave-induced organic reaction enhancement (MORE) chemistry. Part 13. Microwave-assisted rapid and simplified hydrogenation [J].
Banik, BK ;
Barakat, KJ ;
Wagle, DR ;
Manhas, MS ;
Bose, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :5746-5753