Enantioselective syntheses of tremulenediol A and tremulenolide A

被引:29
|
作者
Ashfeld, Brandon L. [1 ]
Martin, Stephen F. [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1016/j.tet.2006.05.087
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise entry to the skeleton of the tremulane sesquiterpenes is described that culminated in the first enantioselective syntheses of tremulenediol A and tremulenolide A. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium(II)-catalyzed intramolecular cyclopropanation followed by a regioselective allylic alkylation and a diastereoseleclive rhodium(l)-catalyzed [5+2] cycloaddition. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10497 / 10506
页数:10
相关论文
共 50 条
  • [31] Racemic and enantioselective syntheses of wine lactone
    Ippoliti, J. Thomas
    Moen, Matthew J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [32] Efficient Enantioselective Syntheses of (+)-Dalesconol A and B
    Zhao, Guoqing
    Xu, Guangqing
    Qian, Chao
    Tang, Wenjun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (09) : 3360 - 3363
  • [33] Recent Developments in the Enantioselective Syntheses of Cyclopropanes
    Inst. für Organische Chemie Der, Technischen Universität, D-01062 Dresden, Germany
    Angew Chem (Int Ed Engl), 9 (971-973):
  • [34] Enantioselective Total Syntheses of Trichodermamides A and B
    Wan, Xiaobo
    Joullie, Madeleine M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (51) : 17236 - +
  • [35] Enantioselective total syntheses of trichodermamides A and B
    Wan, Xiaobo
    Joullié, Madeleine M.
    Journal of the American Chemical Society, 2008, 130 (51): : 17236 - 17237
  • [36] Enantioselective and diastereoselective syntheses of cyanohydrin carbonates
    Belokon, Yuri N.
    Clegg, William
    Harrington, Ross W.
    Ishibashi, Eisuke
    Nomura, Hiroshi
    North, Michael
    TETRAHEDRON, 2007, 63 (39) : 9724 - 9740
  • [37] Enantioselective syntheses of decursinol angelate and decursin
    Lim, J
    Kim, IH
    Kim, HH
    Ahn, KS
    Han, H
    TETRAHEDRON LETTERS, 2001, 42 (24) : 4001 - 4003
  • [38] Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine
    Ghosh, Arun K.
    Born, Joshua R.
    Kassekert, Luke A.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09): : 5167 - 5175
  • [39] Efficient Enantioselective Syntheses of (+)-Dalesconol A and B
    Tang, Wenjun (tangwenjun@sioc.ac.cn), 1600, American Chemical Society (139):
  • [40] Enantioselective and Collective Total Syntheses of Xanthanolides
    Feng, Juan
    Lei, Xiaoqiang
    Bao, Ruiyang
    Li, Yuanhe
    Xiao, Chengqian
    Hu, Lihong
    Tang, Yefeng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) : 16323 - 16327