Stereoselective synthesis of cytoxazone and its analogues

被引:33
作者
Grajewska, Agnieszka [1 ]
Rozwadowska, Maria D. [1 ]
机构
[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
关键词
CYTOKINE MODULATOR; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC EPOXIDATION; BETA-AMINO; (-)-CYTOXAZONE; (+)-EPI-CYTOXAZONE; COMPLEX;
D O I
10.1016/j.tetasy.2007.03.027
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A variety of synthetic routes to (-)-cytoxazone 1, a cytokine modulator isolated from Streptomyces cultures, and its stereomers 2 and regioisomers 3 have been reviewed. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:803 / 813
页数:11
相关论文
共 25 条
[1]   Short-step and scalable synthesis of (±)-cytoxazone [J].
Asano, M ;
Nagasawa, C ;
Suzuki, M ;
Nishiyama, S ;
Sugai, T .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2005, 69 (01) :145-148
[2]  
BIRAMN VB, 2006, J AM CHEM SOC, V128, P6536
[3]   Highly regioselective ring opening of epoxides using NaN3:: a short and efficient synthesis of (-)-cytoxazone [J].
Boruwa, J ;
Borah, JC ;
Kalita, B ;
Barua, NC .
TETRAHEDRON LETTERS, 2004, 45 (39) :7355-7358
[4]   Expanding synthetic utilities of asymmetric dihydroxylation reaction:: Conversion of syn-diols to syn-amino alcohols [J].
Cho, GY ;
Ko, SY .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8745-8747
[5]   Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone [J].
Davies, SG ;
Hughes, DG ;
Nicholson, RL ;
Smith, AD ;
Wright, AJ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (10) :1549-1553
[6]   NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity:: a short route to (-)-cytoxazone and droxidopa [J].
George, Shyla ;
Narina, Srinivasarao V. ;
Sudalai, Arumugam .
TETRAHEDRON LETTERS, 2007, 48 (08) :1375-1378
[7]  
Hamersak Z, 2001, SYNTHESIS-STUTTGART, P1989
[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]   Stereoselective synthesis of (-)-cytoxazone and (+)-5-epi-cytoxazone [J].
Kumar, AR ;
Bhaskar, G ;
Madhan, A ;
Rao, BV .
SYNTHETIC COMMUNICATIONS, 2003, 33 (16) :2907-2916