SYNTHETIC CONVERSION OF BRYOSTATIN-2 TO BRYOSTATIN-1 AND RELATED BRYOPYRANS

被引:17
作者
PETTIT, GR
SENGUPTA, D
HERALD, CL
SHARKEY, NA
BLUMBERG, PM
机构
[1] ARIZONA STATE UNIV,DEPT CHEM,TEMPE,AZ 85287
[2] NCI,LCCTP,MOLEC MECH TUMOR PROMOT SECT,BETHESDA,MD 20892
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1991年 / 69卷 / 05期
关键词
BRYOSTATIN 2-]1; SELECTIVE CONVERSION; BRYOSTATINS-4; AND; 5; PIVALATES;
D O I
10.1139/v91-126
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bryostatin 2 (1a) has been converted to bryostatin 1 (1e) and bryostatin 12 (1i) by a selective protection and deprotection involving the C-26 hydroxyl group. The new bryostatins 1g, 1k, and 1m were also prepared starting from bryostatin 2. The C-7 substituents of natural bryostatins 4 and 5 were revised from isovalerate --> pivalate employing comparative H-1 and C-13 NMR studies of the semi-synthetic bryostatins 1k and 1m and the natural products.
引用
收藏
页码:856 / 860
页数:5
相关论文
共 30 条
[1]  
BLUMBERG PM, 1988, CANCER RES, V48, P1
[2]   SECONDARY METABOLITES FROM MARINE BRYOZOANS - A REVIEW [J].
CHRISTOPHERSEN, C .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1985, 39 (07) :517-529
[3]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[4]   DEMONSTRATION OF SUB-NANOMOLAR AFFINITY OF BRYOSTATIN-1 FOR THE PHORBOL ESTER RECEPTOR IN RAT-BRAIN [J].
DEVRIES, DJ ;
HERALD, CL ;
PETTIT, GR ;
BLUMBERG, PM .
BIOCHEMICAL PHARMACOLOGY, 1988, 37 (21) :4069-4073
[5]   BRYOSTATIN-1, AN ACTIVATOR OF PROTEIN KINASE-C, MIMICS AS WELL AS INHIBITS BIOLOGICAL EFFECTS OF THE PHORBOL ESTER TPA INVIVO AND INVITRO [J].
GSCHWENDT, M ;
FURSTENBERGER, G ;
ROSEJOHN, S ;
ROGERS, M ;
KITTSTEIN, W ;
PETTIT, GR ;
HERALD, CL ;
MARKS, F .
CARCINOGENESIS, 1988, 9 (04) :555-562
[6]  
HASSNER A, 1978, TETRAHEDRON LETT, P4475
[7]   BRYOSTATIN-1, AN ACTIVATOR OF PROTEIN-KINASE-C, INHIBITS TUMOR PROMOTION BY PHORBOL ESTERS IN SENCAR MOUSE SKIN [J].
HENNINGS, H ;
BLUMBERG, PM ;
PETTIT, GR ;
HERALD, CL ;
SHORES, R ;
YUSPA, SH .
CARCINOGENESIS, 1987, 8 (09) :1343-1346
[8]  
HESS AD, 1988, J IMMUNOL, V141, P3263
[9]  
HOLFE G, 1978, ANGEW CHEM INT EDIT, V17, P569
[10]  
HOLZAPFEL CW, 1983, J NAT PRODUCTS, V46, P917