Total synthesis of (+)-pramanicin and stereochemical elucidation of the natural product

被引:28
作者
Barrett, AGM [1 ]
Head, J
Smith, ML
Stock, NS
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England
[2] Celltech Ltd, Therapeut, Slough SL1 4EN, Berks, England
关键词
D O I
10.1039/a807988i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Total synthesis of (+)-pramanicin is achieved through a 'one pot' Michael addition of an aminosilyl zincate species to an alpha,beta-unsaturated lactam and quenching of the resultant enolate with an alpha,beta-unsaturated gamma,delta-epoxy aldehyde.
引用
收藏
页码:133 / 134
页数:2
相关论文
共 9 条
[1]   Nickel-catalyzed hydroxylation of 1,3-dicarbonyl compounds by dimethyldioxirane [J].
Adam, W ;
Smerz, AK .
TETRAHEDRON, 1996, 52 (16) :5799-5804
[2]   Selective removal of the N-BOC protective group using silica gel at low pressure [J].
Apelqvist, T ;
Wensbo, D .
TETRAHEDRON LETTERS, 1996, 37 (09) :1471-1472
[3]   Synthesis of the fatty acid of pramanicin [J].
Cow, C ;
Valentini, D ;
Harrison, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (06) :884-889
[4]   The biosynthesis of pramanicin: intact incorporation of serine and absolute configuration of the antibiotic [J].
Duspara, P ;
Jenkins, SI ;
Hughes, DW ;
Harrison, PHM .
CHEMICAL COMMUNICATIONS, 1998, (23) :2643-2644
[5]  
FLEMING R, 1995, J CHEM SOC P1, P317
[6]   The biosynthesis of pramanicin: origin of the carbon skeleton [J].
Harrison, PHM ;
Hughes, DW ;
Riddoch, RW .
CHEMICAL COMMUNICATIONS, 1998, (02) :273-274
[7]   IMPROVED PROTOCOLS FOR THE SELECTIVE DEPROTECTION OF TRIALKYLSILYL ETHERS USING FLUOROSILICIC ACID [J].
PILCHER, AS ;
DESHONG, P .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5130-5134
[8]   PRAMANICIN, A NOVEL ANTIMICROBIAL AGENT FROM A FUNGAL FERMENTATION [J].
SCHWARTZ, RE ;
HELMS, GL ;
BOLESSA, EA ;
WILSON, KE ;
GIACOBBE, RA ;
TKACZ, JS ;
BILLS, GF ;
LIESCH, JM ;
ZINK, DL ;
CUROTTO, JE ;
PRAMANIK, B ;
ONISHI, JC .
TETRAHEDRON, 1994, 50 (06) :1675-1686
[9]   SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .20. HYDROGEN-PEROXIDE OXIDATION OF THE SILICON-CARBON BOND IN ORGANOALKOXYSILANES [J].
TAMAO, K ;
ISHIDA, N ;
TANAKA, T ;
KUMADA, M .
ORGANOMETALLICS, 1983, 2 (11) :1694-1696