RADICAL CYCLIZATION TO APORPHINES - A NEW, EFFICIENT TOTAL SYNTHESIS OF THE APORPHINE GLAUCINE AND THE 4,5-DIOXOAPORPHINE PONTEVEDRINE, AND THE FIRST TOTAL SYNTHESIS OF 5-OXOAPORPHINES

被引:27
作者
ESTEVEZ, JC [1 ]
VILLAVERDE, MC [1 ]
ESTEVEZ, RJ [1 ]
CASTEDO, L [1 ]
机构
[1] UNIV SANTIAGO COMPOSTELA,FAC QUIM,DEPT QUIM ORGAN,E-15706 SANTIAGO,SPAIN
关键词
D O I
10.1016/S0040-4020(01)85073-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe the radical cyclization of bromobenzylisoquinolines and benzylisoquinolin-3-ones, which afford aporphines or the novel 5-oxoaporphines and 5-oxodehydroaporphines respectively. Oxidation of the latter compounds provides a new route to 4,5-dioxoaporphines.
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页码:2107 / 2114
页数:8
相关论文
共 22 条
  • [1] INTERMOLECULAR BENZYNE CYCLOADDITION APPROACH TO APORPHINOIDS - TOTAL SYNTHESES OF NORCEPHARADIONE-B, CEPHARADIONE-B, DEHYDROANONAINE, DUGUENAINE, DEHYDRONORNUCIFERINE, PONTEVEDRINE, O-METHYLATHEROLINE, LYSICAMINE, AND ALKALOID PO-3
    ATANES, N
    CASTEDO, L
    GUITIAN, E
    SAA, C
    SAA, JM
    SUAU, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) : 2984 - 2988
  • [2] BICK IRC, 1971, TETRAHEDRON LETT, P4795
  • [3] CHEMISTRY OF BRAZILIAN MONIMIACEAE - OXOAPORPHINE ALKALOIDS FROM FUSEA-LONGIFOLIA AND SIPARUNA-GUIANENSIS
    BRAZ FILHO, R
    GABRIEL, SJ
    GOMES, CMR
    GOTTLIEB, OR
    BICHARA, MDGA
    MAIA, JGS
    [J]. PHYTOCHEMISTRY, 1976, 15 (07) : 1187 - 1188
  • [4] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES
    BRINGMANN, G
    WALTER, R
    WEIRICH, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09): : 977 - 991
  • [5] SYNTHESIS OF 1-BENZYLIDENEISOQUINOLINE-3,4-DIONES
    CASTEDO, L
    ESTEVEZ, RJ
    SAA, JM
    SUAU, R
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (06) : 1469 - 1472
  • [6] PHOTOCHEMICAL APPROACH TO 4,5-DIOXOAPORPHINE ALKALOIDS - THE TOTAL SYNTHESIS OF PONTEVEDRINE
    CASTEDO, L
    ESTEVEZ, RJ
    SAA, JM
    SUAU, R
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (06) : 1319 - 1323
  • [7] CASTEDO L, 1980, QUIM SER C, V76, P171
  • [8] PHOTOCHEMICAL ROUTES TO APORPHINES . NEW SYNTHESES OF NUCIFERINE AND GLAUCINE
    CAVA, MP
    MITCHELL, MJ
    HAVLICEK, SC
    LINDERT, A
    SPANGLER, RJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (01) : 175 - &
  • [9] CAVE A, 1989, ALKALOIDS, V35
  • [10] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1.
    CURRAN, DP
    [J]. SYNTHESIS-STUTTGART, 1988, (06): : 417 - 439