SYNTHETIC STUDIES OF THE ANGUCYCLINE ANTIBIOTICS - REACTION OF A QUINONE METHIDE PRODUCED FROM A BENZ[A]ANTHRACENE WITH MOLECULAR-OXYGEN

被引:30
作者
KIM, KJ [1 ]
REIBENSPIES, J [1 ]
SULIKOWSKI, G [1 ]
机构
[1] TEXAS A&M UNIV SYST, DEPT CHEM, COLL STN, TX 77843 USA
关键词
D O I
10.1021/jo00047a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Molecular oxygen-based procedures for the stereocontrolled introduction of oxygen functionality present in the antitumor antibiotics aquayamycin (1) and SF 2315B (2) are described.
引用
收藏
页码:5557 / 5559
页数:3
相关论文
共 22 条
[1]   EFFECT OF ALLYLIC SUBSTITUENTS ON THE FACE SELECTIVITY OF DIELS-ALDER REACTIONS OF SEMICYCLIC DIENES [J].
DATTA, SC ;
FRANCK, RW ;
TRIPATHY, R ;
QUIGLEY, GJ ;
HUANG, L ;
CHEN, S ;
SIHAED, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8472-8478
[2]   ON THE INTRAMOLECULARITY OF THE VITAMIN-K MODEL OXIDATION [J].
DOWD, P ;
HAM, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9403-9404
[3]   METABOLIC PRODUCTS OF MICROORGANISMS .234. URDAMYCINS, NEW ANGUCYCLINE ANTIBIOTICS FROM STREPTOMYCES-FRADIAE .1. ISOLATION, CHARACTERIZATION AND BIOLOGICAL PROPERTIES [J].
DRAUTZ, H ;
ZAHNER, H ;
ROHR, J ;
ZEECK, A .
JOURNAL OF ANTIBIOTICS, 1986, 39 (12) :1657-1669
[4]   REACTION OF THE QUINONE METHIDE FROM REDUCTIVE GLYCOSIDIC CLEAVAGE OF DAUNOMYCIN WITH MOLECULAR-OXYGEN - EVIDENCE FOR SEMIQUINONE METHIDE FORMATION [J].
GAUDIANO, G ;
KOCH, TH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9423-9425
[5]   STUDIES ON THE ISOTETRACENONE ANTIBIOTICS .1. CAPOAMYCIN, A NEW ANTITUMOR ANTIBIOTIC [J].
HAYAKAWA, Y ;
IWAKIRI, T ;
IMAMURA, K ;
SETO, H ;
OTAKE, N .
JOURNAL OF ANTIBIOTICS, 1985, 38 (07) :957-959
[6]   THE STRUCTURES OF NEW ISOTETRACENONE ANTIBIOTICS, KERRIAMYCINS A, B AND C [J].
HAYAKAWA, Y ;
FURIHATA, K ;
SETO, H ;
OTAKE, N .
TETRAHEDRON LETTERS, 1985, 26 (29) :3475-3478
[7]   STUDIES ON THE ISOTETRACENONE ANTIBIOTICS .2. KERRIAMYCIN-A, KERRIAMYCIN-B, AND KERRIAMYCIN-C NEW ANTITUMOR ANTIBIOTICS [J].
HAYAKAWA, Y ;
IWAKIRI, T ;
IMAMURA, K ;
SETO, H ;
OTAKE, N .
JOURNAL OF ANTIBIOTICS, 1985, 38 (07) :960-963
[8]   REGIOSPECIFIC SYNTHESIS OF BROMOJUGLONE DERIVATIVES [J].
HEINZMAN, SW ;
GRUNWELL, JR .
TETRAHEDRON LETTERS, 1980, 21 (45) :4305-4308
[9]   DERIVATIVES OF SAQUAYAMYCIN-A AND SAQUAYAMYCIN-B REGIOSELECTIVE AND DIASTEREOSELECTIVE ADDITION OF ALCOHOLS TO THE L-ACULOSE MOIETY [J].
HENKEL, T ;
ZEECK, A .
JOURNAL OF ANTIBIOTICS, 1990, 43 (07) :830-837
[10]   MECHANISM OF BROMINATION OF 1,5-DIACETOXYNAPHTHALENE [J].
JUNG, ME ;
HAGENAH, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5359-5361