Stereoselective synthesis of the C14-C26 fragment of the cytotoxic macrolide FD-891

被引:6
作者
Murga, J
García-Fortanet, J
Carda, M
Marco, JA [1 ]
机构
[1] Univ Jaume 1, Dept Quim Inorgan & Organ, E-12080 Castellon de La Plana, Spain
[2] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain
关键词
macrolides; cytotoxicity; FD-891; asymmetric allylboration; boron aldol reactions;
D O I
10.1016/j.tetlet.2004.08.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective synthesis of the C-14-C-26 fragment of the naturally occurring, cytotoxic macrolide FD-891, is described. Asymmetric Evans aldol reactions and aldehyde Brown allylations are key steps of the synthesis. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7499 / 7501
页数:3
相关论文
共 19 条
[1]  
[Anonymous], [No title captured]
[2]  
[Anonymous], 1997, ORG REACT
[3]  
Bartra M., 1993, RECENT PROGR CHEM SY, V2, P1
[4]   SYNTHESIS OF THE LOWER SUBUNIT OF RHIZOXIN [J].
BOGER, DL ;
CURRAN, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2235-2244
[5]   VERSATILE ALPHA-PINENE-BASED BORANE REAGENTS FOR ASYMMETRIC SYNTHESES [J].
BROWN, HC ;
RAMACHANDRAN, PV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 500 (1-2) :1-19
[6]   Towards a synthesis of epothilone A: asymmetric synthesis of C(1)-C(6) and C(7)-(15) fragments [J].
Chandrasekhar, S ;
Reddy, CR .
TETRAHEDRON-ASYMMETRY, 2002, 13 (03) :261-268
[7]   A divergent approach to apoptolidin and FD-891: asymmetric preparation of a common intermediate [J].
Chng, SS ;
Xu, J ;
Loh, TP .
TETRAHEDRON LETTERS, 2003, 44 (27) :4997-5000
[8]   Stereostructure of a novel cytotoxic 18-membered macrolactone antibiotic FD-891 [J].
Eguchi, T ;
Kobayashi, K ;
Uekusa, H ;
Ohashi, Y ;
Mizoue, K ;
Matsushima, Y ;
Kakinuma, K .
ORGANIC LETTERS, 2002, 4 (20) :3383-3386
[9]   The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride.: The merged stereochemical impact of α- and β-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles [J].
Evans, DA ;
Allison, BD ;
Yang, MG ;
Masse, CE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10840-10852
[10]  
Greene T.W., 1999, PROTECTIVE GROUPS OR, V3rd, P27