A Diels-Alder strategy towards a benzonaphthopyranoquinone

被引：11
|
作者：
Tapia, RA
Alegría, L
Valderrama, JA
Cortés, M
Pautet, F
Fillion, H
机构：
[1] Pontificia Univ Catolica Chile, Fac Quim, Santiago 22, Chile
[2] Univ Lyon 1, Fac Pharm, Chim Organ Lab, F-69373 Lyon 08, France
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 05期
关键词：
Diels-Alder reaction; quinone; benzopyran;
D O I：
10.1016/S0040-4039(00)02150-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of a suitably protected aryllithium derivative with citral, and subsequent deprotection and cyclization was used to obtain dibenzopyran 5, a precursor of the tricyclic quinone 6. Diels-Alder reaction of 6 with 1,3-dimethoxy-1-trimethylsilyloxy-1,3-butadiene 7 led to befizonaphthopyranoquinone 8. The regioselectivity in the dienophilic partner is governed by the remote oxygen of the pyran ring. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：887 / 889
页数：3
相关论文
共 50 条
  • [31] A STRATEGY FOR INTERMOLECULAR DIELS-ALDER CYCLO-ADDITION TO ENAMIDES
    BAULD, NL
    HARIRCHIAN, B
    REYNOLDS, DW
    WHITE, JC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) : 8111 - 8117
  • [32] Fabrication of Maleimide Containing Thiol Reactive Hydrogels via Diels-Alder/Retro-Diels-Alder Strategy
    Kosif, Irem
    Park, Eun-Ju
    Sanyal, Rana
    Sanyal, Amitav
    MACROMOLECULES, 2010, 43 (09) : 4140 - 4148
  • [33] INVERSE DIELS-ALDER ADDITIONS .10. INVERSE DIELS-ALDER ADDITIONS WITH HETERODIENOPHILES
    SEITZ, G
    OVERHEU, W
    CHEMIKER-ZEITUNG, 1979, 103 (06): : 230 - 231
  • [34] DIELS-ALDER REACTIONS OF CYCLOALKENONES .19. DIELS-ALDER REACTIONS OF SOME CARENONES
    MINUTI, L
    RADICS, L
    TATICCHI, A
    VENTURINI, L
    WENKERT, E
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14): : 4261 - 4265
  • [35] Chiral anthracenes as a Diels-Alder/retro Diels-Alder template in asymmetric synthesis.
    Sanyal, A
    Snyder, JK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U121 - U121
  • [36] ISOMERISM IN THE DIELS-ALDER REACTION .3. THE BROMINATION OF THE DIELS-ALDER ADDUCT, NORBORNYLENE
    KWART, H
    KAPLAN, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (16) : 4072 - 4077
  • [37] DIELS-ALDER REACTIONS OF CYCLOALKENONES .18. UNUSUAL DIELS-ALDER REACTIONS OF EUCARVONE
    GUO, M
    MINUTI, L
    TATICCHI, A
    WENKERT, E
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04): : 1366 - 1368
  • [38] DIELS-ALDER REACTIONS OF THEBAINES WITH CYCLOALKENONES - LITHIUM TETRAFLUOROBORATE AS A NOVEL DIELS-ALDER CATALYST
    BARTON, JW
    COOP, A
    LEWIS, JW
    TETRAHEDRON LETTERS, 1993, 34 (42) : 6777 - 6778
  • [39] Diels-Alder reactions of fullerenes
    Sliwa, W
    FULLERENE SCIENCE AND TECHNOLOGY, 1997, 5 (06): : 1133 - 1175
  • [40] DIELS-ALDER REACTIONS OF PIPERYLENES
    BROCKSOM, TJ
    CONSTANTINO, MG
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (18): : 3450 - 3453
12345