PALLADIUM-CATALYZED COUPLING OF 2-BROMONAPHTHOQUINONES WITH STANNANES - A CONCISE SYNTHESIS OF ANTIBIOTICS WS-5995-A AND WS-5995-C AND RELATED-COMPOUNDS

被引:63
作者
TAMAYO, N [1 ]
ECHAVARREN, AM [1 ]
PAREDES, MC [1 ]
机构
[1] CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
关键词
D O I
10.1021/jo00023a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of antibiotics WS 5995 A and C and a hypothetical intermediate in the biosynthesis of the kinamycin antibiotics have been completed by using as the key step the palladium-catalyzed coupling of 2-bromo-1,4-naphthoquinones with stannanes.
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页码:6488 / 6491
页数:4
相关论文
共 43 条
[11]   TOTAL SYNTHESIS OF PHENANTHROVIRIDIN AGLYCON - THE 1ST NATURALLY-OCCURRING BENZO[B]PHENANTHRIDINE [J].
GORE, MP ;
GOULD, SJ ;
WELLER, DD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2289-2291
[12]   THE FORMAL OXIDATIVE ADDITION OF ELECTRON-RICH TRANSOID DIENES TO BROMONAPHTHOQUINONES [J].
GRUNWELL, JR ;
KARIPIDES, A ;
WIGAL, CT ;
HEINZMAN, SW ;
PARLOW, J ;
SURSO, JA ;
CLAYTON, L ;
FLEITZ, FJ ;
DAFFNER, M ;
STEVENS, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :91-95
[13]   REGIOSPECIFIC SYNTHESIS OF BROMOJUGLONE DERIVATIVES [J].
HEINZMAN, SW ;
GRUNWELL, JR .
TETRAHEDRON LETTERS, 1980, 21 (45) :4305-4308
[14]  
HUA DH, 1990, SYNLETT, P233
[15]   NEW ANTICOCCIDIAL ANTIBIOTICS, WS-5995-A AND WS-5995-B .1. ISOLATION AND CHARACTERIZATION [J].
IKUSHIMA, H ;
OKAMOTO, M ;
TANAKA, H ;
OHE, O ;
KOHSAKA, M ;
AOKI, H ;
IMANAKA, H .
JOURNAL OF ANTIBIOTICS, 1980, 33 (10) :1107-1113
[16]   STRUCTURE AND SYNTHESIS OF NEW ANTICOCCIDIAL ANTIBIOTICS ISOLATED FROM STREPTOMYCES AURANTICOLOR [J].
IKUSHIMA, H ;
TAKASE, S ;
KAWAI, Y ;
ITOH, Y ;
OKAMOTO, M ;
TANAKA, H ;
IMANAKA, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1983, 47 (10) :2231-2235
[17]   STREPTOMYCES-AURANTICOLOR SP-NOV A NEW ANTICOCCIDIAL ANTIBIOTICS PRODUCER [J].
IKUSHIMA, H ;
IGUCHI, E ;
KOHSAKA, M ;
AOKI, H ;
IMANAKA, H .
JOURNAL OF ANTIBIOTICS, 1980, 33 (10) :1103-1106
[18]   TOTAL SYNTHESIS OF THE AGLYCONE OF THE 8-METHYL BENZONAPHTHOPYRONE ANTIBIOTICS, GILVOCARCIN-M, VIRENOMYCIN-M, AND ALBACARCIN-M [J].
JUNG, ME ;
JUNG, YH .
TETRAHEDRON LETTERS, 1988, 29 (21) :2517-2520
[19]   MECHANISM OF BROMINATION OF 1,5-DIACETOXYNAPHTHALENE [J].
JUNG, ME ;
HAGENAH, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5359-5361
[20]  
KELLY TR, 1984, TETRAHEDRON LETT, V25, P2127, DOI 10.1016/S0040-4039(01)81179-5