First total synthesis of the whole series of the antiostatins A and B

被引:85
作者
Knott, Kerstin E. [1 ]
Auschill, Stefan [1 ]
Jaeger, Anne [1 ]
Knoelker, Hans-Joachim [1 ]
机构
[1] Tech Univ Dresden, Dept Chem, D-01069 Dresden, Germany
关键词
TRANSITION-METAL-COMPLEXES; ORGANIC-SYNTHESIS; ANTIOXIDATIVE AGENTS; CONVERSION; CHEMISTRY; ACID;
D O I
10.1039/b821039j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first synthesis of the whole antiostatin family is described by using an iron-mediated carbazole synthesis, regioselective nitration at C-4 and establishing 5-isobutyl-1-nitrobiuret as a reagent for introduction of the antiostatin B side chain at C-4.
引用
收藏
页码:1467 / 1469
页数:3
相关论文
共 28 条
[1]   A stereoselective synthesis for the (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid and its monounsaturated analog (Z)-14-methyl-9-pentadecenoic acid [J].
Carballeira, NM ;
Sanabria, D ;
Ayala, NL ;
Cruz, C .
TETRAHEDRON LETTERS, 2004, 45 (19) :3761-3763
[2]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[3]  
Choshi T, 1996, HETEROCYCLES, V43, P1847
[4]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[5]   The oxidation of tribromoresorcinol [J].
Davis, TL ;
Hill, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1929, 51 (1-4) :493-504
[6]   Studies in the urea series XIII Alkyl-nitroureas and alkyl-nitrobiurets [J].
Davis, TL ;
Constan, ND .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :1800-1803
[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]  
DETWEILER WK, 1951, J AM CHEM SOC, V73, P5451, DOI 10.1021/ja01155a515
[9]   ANTICONVULSANT DRUGS .6. SOME 1-SUBSTITUTED BIURETS [J].
DUNNIGAN, DA ;
CLOSE, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3615-3616
[10]   Novel indole chemistry in the synthesis of heterocycles [J].
Gribble, GW ;
Saulnier, MG ;
Pelkey, ET ;
Kishbaugh, TLS ;
Liu, YB ;
Jiang, J ;
Trujillo, HA ;
Keavy, DJ ;
Davis, DA ;
Conway, SC ;
Switzer, FL ;
Roy, S ;
Silva, RA ;
Obaza-Nutaitis, JA ;
Sibi, MP ;
Moskalev, NV ;
Barden, TC ;
Chang, L ;
Habeski, WM ;
Pelcman, B ;
Sponholtz, WR ;
Chau, RW ;
Allison, BD ;
Garaas, SD ;
Sinha, MS ;
McGowan, MA ;
Reese, MR ;
Harpp, KS .
CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1493-1519