The first synthesis of the Streptomyces derived antibiotic U-62162

被引:7
作者
Alcaraz, L [1 ]
Taylor, RJK [1 ]
机构
[1] Univ York, Dept Chem, York YO1 5DD, N Yorkshire, England
关键词
D O I
10.1039/a801265b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
U-62162, a member of the manumycin family of antibiotics, has been prepared as a mixture of diastereoisomers and shown to contain a syn-hydroxy epoxide nucleus and a 1,3-syn-disposed dimethyl unit in the upper side chain; the cornerstone of the synthetic route utilises organometallic addition to a monoprotected quinone epoxide-the first time this approach has been successfully employed to prepare a manumycin antibiotic.
引用
收藏
页码:1157 / 1158
页数:2
相关论文
共 17 条
[1]   The first total synthesis of a member of the manumycin family of antibiotics: Alisamycin [J].
Alcaraz, L ;
Macdonald, G ;
Kapfer, I ;
Lewis, NJ ;
Taylor, RJK .
TETRAHEDRON LETTERS, 1996, 37 (36) :6619-6622
[2]  
ALCARAZ L, IN PRESS J ORG CHEM
[3]  
BUZZETTI F, 1963, PHARM ACTA HELV, V38, P871
[4]   ON THE STRUCTURE OF ALISAMYCIN, A NEW MEMBER OF THE MANUMYCIN CLASS OF ANTIBIOTICS [J].
CHATTERJEE, S ;
VIJAYAKUMAR, EKS ;
FRANCO, CMM ;
BLUMBACH, J ;
GANGULI, BN .
JOURNAL OF ANTIBIOTICS, 1993, 46 (06) :1027-1030
[5]   Natural products derived from unusual variants of the shikimate pathway [J].
Floss, HG .
NATURAL PRODUCT REPORTS, 1997, 14 (05) :433-452
[6]   Acetal and ketal deprotection using montmorillonite K10: The first synthesis of syn-4,8-dioxatricyclo[5.1.0.0(3,5)]-2,6-octanedione [J].
Gautier, ECL ;
Graham, AE ;
McKillop, A ;
Standen, SP ;
Taylor, RJK .
TETRAHEDRON LETTERS, 1997, 38 (11) :1881-1884
[7]   NISAMYCIN, A NEW MANUMYCIN GROUP ANTIBIOTIC FROM STREPTOMYCES SP K106 .2. STRUCTURE DETERMINATION AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
HAYASHI, K ;
NAKAGAWA, M ;
FUJITA, T ;
TANIMORI, S ;
NAKAYAMA, M .
JOURNAL OF ANTIBIOTICS, 1994, 47 (10) :1110-1115
[8]   NISAMYCIN, A NEW MANUMYCIN GROUP ANTIBIOTIC FROM STREPTOMYCES SP K106 .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES [J].
HAYASHI, K ;
NAKAGAWA, M ;
NAKAYAMA, M .
JOURNAL OF ANTIBIOTICS, 1994, 47 (10) :1104-1109
[9]   ABSOLUTE STEREOCHEMISTRY OF ALISAMYCIN [J].
HAYASHI, K ;
NAKAGAWA, M ;
FUJITA, T ;
NAKAYAMA, M .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1994, 58 (07) :1332-1333
[10]   3-amino-4-hydroxybenzoic acid: The precursor of the C7N unit in asukamycin and manumycin [J].
Hu, YD ;
Melville, CR ;
Gould, SJ ;
Floss, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4301-4302