Synthetic study of tautomycetin: Synthesis of two large subunits

被引:12
作者
Oikawa, H
Yoneta, Y
Ueno, T
Oikawa, M
Wakayama, T
Ichihara, A
机构
[1] Dept. of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
[2] Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560
关键词
tautomycetin; tautomycin; protein phosphatase inhibitor;
D O I
10.1016/S0040-4039(97)10100-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two large subunits for synthesis of tautomycetin have been synthesized. Efficient construction of the dienone moiety has been achieved by regioselective hydrostannylation of an internal alkyne and subsequent Stille coupling. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7897 / 7900
页数:4
相关论文
共 21 条
[2]  
CHENG XC, 1990, J ANTIBIOT, V43, P809, DOI 10.7164/antibiotics.43.809
[3]   A NEW ANTIBIOTIC, TAUTOMYCIN [J].
CHENG, XC ;
KIHARA, T ;
KUSAKABE, H ;
MAGAE, J ;
KOBAYASHI, Y ;
FANG, RP ;
NI, ZF ;
SHEN, YC ;
KO, K ;
YAMAGUCHI, I ;
ISONO, K .
JOURNAL OF ANTIBIOTICS, 1987, 40 (06) :907-909
[4]   THE STRUCTURE OF TAUTOMYCETIN, A DIALKYLMALEIC ANHYDRIDE ANTIBIOTIC [J].
CHENG, XC ;
UBUKATA, M ;
ISONO, K .
JOURNAL OF ANTIBIOTICS, 1990, 43 (07) :890-896
[5]  
CHENG XC, 1989, J ANTIBIOT, V42, P141
[6]   Determination of the C-7, 9, 12, 13, 17 and 18 stereochemistries of tautomycetin. Synthesis of the tautomycetin degradation product [J].
Dai, JP ;
Sodeoka, M ;
Shibasaki, M .
TETRAHEDRON LETTERS, 1996, 37 (04) :491-494
[7]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[8]   ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].
HORITA, K ;
YOSHIOKA, T ;
TANAKA, T ;
OIKAWA, Y ;
YONEMITSU, O .
TETRAHEDRON, 1986, 42 (11) :3021-3028
[9]   RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].
INANAGA, J ;
HIRATA, K ;
SAEKI, H ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993
[10]   TAUTOMYCIN FROM THE BACTERIUM STREPTOMYCES-VERTICILLATUS - ANOTHER POTENT AND SPECIFIC INHIBITOR OF PROTEIN PHOSPHATASE-1 AND PHOSPHATASE-2A [J].
MACKINTOSH, C ;
KLUMPP, S .
FEBS LETTERS, 1990, 277 (1-2) :137-140