Synthetic applications of the cyclic iminocarbonate rearrangement:: enantioselective syntheses of chloramphenicol and 4-epi-cytoxazone

被引:55
作者
Park, JN
Ko, SY [1 ]
Koh, HY
机构
[1] Ewha Womans Univ, Dept Chem, Seoul 120750, South Korea
[2] Ewha Womans Univ, Div Mol Life Sci, Seoul 120750, South Korea
[3] Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea
关键词
enantioselective synthesis; cyclic iminocarbonate rearrangement; regioselection; chloramphenicol; 4-epi-cytoxazone;
D O I
10.1016/S0040-4039(00)00878-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chloramphenicol and 4-epi-cytoxazone have been enantioselectively synthesized using the asymmetric dihydroxylation and the cyclic iminocarbonate rearrangement as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5553 / 5556
页数:4
相关论文
共 18 条
[1]  
[Anonymous], 1998, STRATEGIES ORGANIC D
[2]  
[Anonymous], CATALYTIC ASYMMETRIC
[3]   Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].
Cardillo, G ;
Tomasini, C .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&
[4]   Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates [J].
Cho, GY ;
Park, JN ;
Ko, SY .
TETRAHEDRON LETTERS, 2000, 41 (11) :1789-1792
[5]  
COLE DC, 1994, TETRAHEDRON, V50, P9517
[6]   SELECTIVE TRANSFORMATIONS OF THREO-2,3-DIHYDROXY ESTERS [J].
FLEMING, PR ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2869-2875
[7]  
Juraristi E, 1994, ALDRICHIM ACTA, V27, P3
[8]   Isolation and biological activity of a novel cytokine modulator, cytoxazone [J].
Kakeya, H ;
Morishita, M ;
Kobinata, K ;
Osono, M ;
Ishizuka, M ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1998, 51 (12) :1126-1128
[9]   Cytoxazone:: A novel cytokine modulator containing a 2-oxazolidinone ring produced by Streptomyces sp. [J].
Kakeya, H ;
Morishita, M ;
Koshino, H ;
Morita, T ;
Kobayashi, K ;
Osada, H .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1052-1053
[10]   AN ACCESS TO ERYTHRO-DIOLS VIA SHARPLESS ASYMMETRIC DIHYDROXYLATION REACTION [J].
KO, SY ;
MALIK, M ;
DICKINSON, AF .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2570-2576