Highly Efficient Gold-Catalyzed Synthesis of Dibenzocycloheptatrienes

被引:36
|
作者
Pflaesterer, Daniel [1 ]
Rettenmeier, Eva [1 ]
Schneider, Severin [1 ]
Ruiz, Edgar de Las Heras [1 ]
Rudolph, Matthias [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
[2] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia
关键词
dibenzocycloheptanoids; gold; hydroarylation; natural products; total synthesis; INTRAMOLECULAR ALKYNE HYDROARYLATION; C-H BONDS; CINNAMOMUM-SUBAVENIUM; HETEROARENES; DERIVATIVES; CYCLIZATION; COMPLEXES; CHEMISTRY; GOLD(III); TUBULIN;
D O I
10.1002/chem.201402015
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dibenzocycloheptatrienes are obtained by a gold-catalyzed 7-exo-dig hydroarylation protocol in a highly efficient manner. The gold-catalyzed reaction usually gives the products in high yields and excellent selectivity. This procedure provides an easy and efficient access to dibenzocycloheptanoids, which are an interesting and unique class of natural products. This was underlined by the first total synthesis of reticuol.
引用
收藏
页码:6752 / 6755
页数:4
相关论文
共 50 条
  • [1] Highly selective gold-catalyzed arene synthesis
    Hashmi, ASK
    Frost, TM
    Bats, JW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11553 - 11554
  • [2] Highly Efficient and Eco-Friendly Gold-Catalyzed Synthesis of Homoallylic Ketones
    Gomez-Suarez, Adrian
    Gasperini, Danila
    Vummaleti, Sai V. C.
    Poater, Albert
    Cavallo, Luigi
    Nolan, Steven P.
    ACS CATALYSIS, 2014, 4 (08): : 2701 - 2705
  • [3] Gold-catalyzed highly enantioselective synthesis of axially chiral allenes
    Lo, Vanessa Kar-Yan
    Wong, Man-Kin
    Che, Chi-Ming
    ORGANIC LETTERS, 2008, 10 (03) : 517 - 519
  • [4] Gold-Catalyzed Synthesis of Iodofulvenes
    Noesel, Pascal
    Lauterbach, Tobias
    Rudolph, Matthias
    Rominger, Frank
    Hashmi, A. Stephen K.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (26) : 8634 - 8641
  • [5] Highly Efficient Heterogeneous Gold-catalyzed Direct Synthesis of Tertiary and Secondary Amines from Alcohols and Urea
    He, Lin
    Qian, Yue
    Ding, Ran-Sheng
    Liu, Yong-Mei
    He, He-Yong
    Fan, Kang-Nian
    Cao, Yong
    CHEMSUSCHEM, 2012, 5 (04) : 621 - 624
  • [6] Straightforward and Highly Efficient Synthesis of -Acetoxy Ketones through Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes
    Wu, Chao
    Liang, Zhiwu
    Yan, Dong
    He, Weimin
    Xiang, Jiannan
    SYNTHESIS-STUTTGART, 2013, 45 (18): : 2605 - 2611
  • [7] Highly efficient gold-catalyzed atom-economical annulation of phenols with dienes
    Nguyen, Rene-Viet
    Yao, Xiaoquan
    Li, Chao-Jun
    ORGANIC LETTERS, 2006, 8 (11) : 2397 - 2399
  • [8] Efficient Synthesis of γ-Lactones via Gold-Catalyzed Tandem Cycloisomerization/Oxidation
    Shu, Chao
    Liu, Meng-Qi
    Sun, Yu-Zhe
    Ye, Long-Wu
    ORGANIC LETTERS, 2012, 14 (18) : 4958 - 4961
  • [9] Gold-Catalyzed Conversion of Highly Strained Compounds
    Li, Deyao
    Zang, Wenqing
    Bird, Melissa J.
    Hyland, Christopher J. T.
    Shi, Min
    CHEMICAL REVIEWS, 2021, 121 (14) : 8685 - 8755
  • [10] Gold-Catalyzed Synthesis of Spirofused Indoloquinuclidines
    Glinsky-Olivier, Nicolas
    Retailleau, Pascal
    Guinchard, Xavier
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (42) : 5823 - 5829