Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives:: Synthesis of the antibiotic CJ-15,801

被引:138
作者
Han, C
Shen, RC
Su, S
Porco, JA
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA
关键词
D O I
10.1021/ol0360041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.
引用
收藏
页码:27 / 30
页数:4
相关论文
共 44 条
[31]   STRUCTURE OF PALYTOXIN [J].
MOORE, RE ;
BARTOLINI, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2491-2494
[32]  
MOORE RE, 1985, PROGR CHEM ORGANIC N, V48, P81
[33]   STUDIES OF COPPER(I) OLEFIN COMPLEXES - FORMATION-CONSTANTS OF COPPER OLEFIN COMPLEXES WITH 2,2'-BIPYRIDINE, 1,10-PHENANTHROLINE, AND THEIR DERIVATIVES [J].
MUNAKATA, M ;
KITAGAWA, S ;
KOSOME, S ;
ASAHARA, A .
INORGANIC CHEMISTRY, 1986, 25 (15) :2622-2627
[34]   A domino copper-catalyzed C-O coupling-Claisen rearrangement process [J].
Nordmann, G ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (17) :4978-4979
[35]   Versatile acylation of N-nucleophiles using a new polymer-supported 1-hydroxybenzotriazole derivative [J].
Pop, IE ;
Deprez, BP ;
Tartar, AL .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2594-2603
[36]   Lobatamide C: Total synthesis, stereochemical assignment, preparation of simplified analogues, and V-ATPase inhibition studies [J].
Shen, RC ;
Lin, CT ;
Bowman, EJ ;
Bowman, BJ ;
Porco, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7889-7901
[37]   Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution [J].
Shen, RC ;
Porco, JA .
ORGANIC LETTERS, 2000, 2 (09) :1333-1336
[38]   Molybdenum-catalyzed allylic substitution. Influence of 1,10-phenanthroline ligands on reactivity and selectivity [J].
Sjogren, MPT ;
Frisell, H ;
Akermark, B ;
Norrby, PO ;
Eriksson, L ;
Vitagliano, A .
ORGANOMETALLICS, 1997, 16 (05) :942-950
[39]   CJ-15,801, a novel antibiotic from a fungus, Seimatosporium sp. [J].
Sugie, Y ;
Dekker, KA ;
Hirai, H ;
Ichiba, T ;
Ishiguro, M ;
Shiomi, Y ;
Sugiura, A ;
Brennan, L ;
Duignan, J ;
Huang, LH ;
Sutcliffe, J ;
Kojima, Y .
JOURNAL OF ANTIBIOTICS, 2001, 54 (12) :1060-1065
[40]   SYNTHESIS OF PALYTOXIN FROM PALYTOXIN CARBOXYLIC-ACID [J].
SUH, EM ;
KISHI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11205-11206