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
  • [41] DIELS-ALDER REACTIONS WITH DIHYDRONAPHTHALENES
    DENO, NC
    CHAFETZ, H
    JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (03): : 449 - 449
  • [42] DIELS-ALDER REACTIONS OF ISOINDOLE
    STEVENS, SR
    SMITH, RG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1978, 176 (SEP): : 2 - 2
  • [43] DIELS-ALDER REACTIONS OF MALEIMIDE
    RAY, FE
    SAWICKI, E
    BORUM, OH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (05) : 1247 - 1249
  • [44] The Diels-Alder Cyclization of Ketenimines
    Erb, Jeremy
    Strull, Jessica
    Miller, David
    He, Jean
    Lectka, Thomas
    ORGANIC LETTERS, 2012, 14 (08) : 2191 - 2193
  • [45] The Diels-Alder reaction: an update
    Brocksom, TJ
    Nakamura, J
    Ferreira, ML
    Brocksom, U
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (05) : 597 - 622
  • [46] KAOLINITE AS A DIELS-ALDER ACCELERATOR
    COLLET, C
    LASZLO, P
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 189 - ORGN
  • [47] DIELS-ALDER REACTION OF CYCLOPROPENYLKETONE
    KOBAYASHI, Y
    YOSHIDA, T
    HANZAWA, Y
    KUMADAKI, I
    TETRAHEDRON LETTERS, 1980, 21 (48) : 4601 - 4604
  • [48] DIELS-ALDER REACTIONS OF PERFLUOROCYCLOPENTADIENE
    BANKS, RE
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (10): : 1372 - &
  • [49] Controlling Diels-Alder reactions
    Safiullah, S
    CHEMISTRY IN BRITAIN, 1996, 32 (11) : 20 - 20
  • [50] DIELS-ALDER REACTIVITY OF VINYLSULFOXYALLENES
    WANG, XH
    DONOVALOVA, J
    HOLLIS, A
    JOHNSON, D
    RODRIGUEZ, A
    KENNEDY, GD
    KRISHNAN, G
    BANKS, H
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (04) : 871 - 876
12345