An aldol-based approach to the synthesis of the antibiotic Anisomycin

被引:41
作者
Hulme, AN [1 ]
Rosser, EM [1 ]
机构
[1] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
关键词
D O I
10.1021/ol017016u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS A new approach to the synthesis of the antibiotic anisomycin is reported that relies upon a key aldol disconnection. The glycolate aldol coupling proceeds in 75% yield and with >95% diastereoselectivity, which allows the 13-step synthesis to proceed in 35% overall yield.
引用
收藏
页码:265 / 267
页数:3
相关论文
共 34 条
[1]   A NITRONE-BASED APPROACH TO THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-ANISOMYCIN [J].
BALLINI, R ;
MARCANTONI, E ;
PETRINI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1316-1318
[2]  
BUCHANAN JG, 1985, J CHEM SOC P1, P486
[3]   Formal total synthesis of enantiopure (-)-anisomycin, antibiotic from Streptomyces [J].
Delair, P ;
Brot, E ;
Kanazawa, A ;
Greene, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1383-1386
[4]   Neurobiology - The shaky trace [J].
Dudai, Y .
NATURE, 2000, 406 (6797) :686-687
[5]   TOTAL SYNTHESIS OF ANTIBIOTIC ANISOMYCIN [J].
FELNER, I ;
SCHENKER, K .
HELVETICA CHIMICA ACTA, 1970, 53 (04) :754-&
[6]   SYNTHESIS OF MEDIUM RING ETHERS .4. STEREOSELECTIVE CLAISEN-MEDIATED RING EXPANSION AS A ROUTE TO HOMOCHIRAL DISUBSTITUTED MEDIUM RING LACTONES [J].
FUHRY, MAM ;
HOLMES, AB ;
MARSHALL, DR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (22) :2743-2746
[7]   Exploratory synthetic studies of the alpha-methoxylation of amides via cuprous ion-promoted decomposition of o-diazobenzamides [J].
Han, G ;
LaPorte, MG ;
McIntosh, MC ;
Weinreb, SM ;
Parvez, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9483-9493
[8]   ANISOMYCIN AND NEW CONGENERS ACTIVE AGAINST HUMAN TUMOR-CELL LINES [J].
HOSOYA, Y ;
KAMEYAMA, T ;
NAGANAWA, H ;
OKAMI, Y ;
TAKEUCHI, T .
JOURNAL OF ANTIBIOTICS, 1993, 46 (08) :1300-1302
[9]   A new approach to (-)-anisomycin [J].
Huang, PQ ;
Wang, SL ;
Ruan, YP ;
Gao, JX .
NATURAL PRODUCT LETTERS, 1998, 11 (02) :101-106
[10]   A flexible and efficient synthesis of the pyrrolidine α-glycosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol (DAB-1) [J].
Hulme, AN ;
Montgomery, CH ;
Henderson, DK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1837-1841