Vinyl quinones as Diels-Alder dienes: Concise synthesis of (-)-halenaquinone

被引：47
|
作者：
Kienzler, Michael A. [1 ]
Suseno, Sandy [1 ]
Trauner, Dirk [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 27期
关键词：
D O I：
10.1021/ja8035042
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A concise asymmetric synthesis of (-)-halenaquinone is described. The synthesis features a diastereoselective Heck cyclization to set a quaternary center as well as a novel intramolecular inverse-electron-demand Diels-Alder reaction I involving a vinyl quinone. The synthesis is highly convergent and features a minimal amount of protecting group manipulations.
引用
收藏
页码：8604 / +
页数：3
相关论文
共 50 条
  • [31] Diels-Alder Reaction of Alantolactone and Isoalantolactone with Conjugated Dienes
    Jia, Y.-Y.
    Xiao, S.-J.
    Dong, T.-W.
    Zhao, P.-Y.
    Huaxue Xuebao/Journal of Chemistry, 1991, 49 (06):
  • [32] DIELS-ALDER REACTIONS OF DIENES WITH ALKYNES CATALYZED BY DIAZADIENEIRON
    DIECK, HT
    DIERCKS, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10): : 778 - 779
  • [33] DIENAMINES AS DIELS-ALDER DIENES - AN EFFICIENT CYCLOHEXANNULATION SEQUENCE
    SNOWDEN, RL
    WUST, M
    TETRAHEDRON LETTERS, 1986, 27 (06) : 699 - 702
  • [34] DIELS-ALDER REACTION OF UNSYMMETRICAL DIENES WITH METHYL ACRYLATE
    ANSELL, MF
    CLEMENTS, AH
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (02): : 275 - &
  • [35] Synthesis and Diels-Alder Cycloadditions of exo-Imidazolidin-2-one Dienes
    Bautista, Rafael
    Bernal, Pablo
    Herrera, Rafael
    Santoyo, Blanca M.
    Miguel Lazcano-Seres, J.
    Delgado, Francisco
    Tamariz, Joaquin
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19): : 7901 - 7911
  • [36] DIELS-ALDER REACTIONS OF ORTHO BENZOQUINONES WITH ACYCLIC DIENES
    ANSELL, MF
    BIGNOLD, AJ
    GOSDEN, AF
    LESLIE, VJ
    MURRAY, RA
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (08): : 1414 - &
  • [37] Extended anthracenes and their use as dienes in Diels-Alder reactions
    Sadeq, Hasnaa
    Thiemann, Thies
    Graham, John P.
    Al Jasem, Yosef
    Bugenhagen, Bernhard
    al Rawashdeh, Nathir
    al Sulaibi, Mazen
    18TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY, 2014,
  • [38] Diels-Alder addition of acyclic dienes to chiral naphthoquinones
    Brimble, MA
    Elliott, RJ
    McEwan, JF
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (07) : 571 - 576
  • [39] THE TRIPLEX DIELS-ALDER REACTION OF INDENE AND CYCLIC DIENES
    CALHOUN, GC
    SCHUSTER, GB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) : 8021 - 8027
  • [40] CHIRAL KETENE ACETALS AS DIENES IN THE DIELS-ALDER REACTION
    BOEHLER, MA
    KONOPELSKI, JP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 231 - ORGN
12345