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
来源：
TETRAHEDRON | 2006年 / 62卷 / 45期
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
  • [21] Recent developments in the enantioselective syntheses of cyclopropanes
    Reissig, HU
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (09): : 971 - 973
  • [22] Enantioselective Total Syntheses of Communesins A and B
    Zuo, Zhiwei
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 12008 - 12011
  • [23] Enantioselective syntheses of (-)- and (+)-homocitric acid lactones
    Rodriguez, GH
    Biellmann, JF
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05): : 1822 - 1824
  • [24] Enantioselective Divergent Syntheses of Diterpenoid Pyrones
    Ji, Yunpeng
    Liu, Yaqian
    Guan, Weiqiang
    Guo, Chuning
    Jia, Hongli
    Hong, Benke
    Li, Houhua
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (13) : 9395 - 9403
  • [25] New camphor derivatives for enantioselective syntheses
    Mellao, ML
    Vasconcellos, MLAA
    TETRAHEDRON-ASYMMETRY, 1996, 7 (06) : 1607 - 1610
  • [26] Enantioselective Total Syntheses of Cyathane Diterpenoids
    Nakada, Masahisa
    CHEMICAL RECORD, 2014, 14 (04): : 641 - 662
  • [27] ENANTIOSELECTIVE SYNTHESES OF CHIRAL HYDROXYLAMINES AND HYDROXYUREAS
    LANTOS, I
    CHIMICA OGGI-CHEMISTRY TODAY, 1995, 13 (09) : 39 - 41
  • [28] Diastereo- and enantioselective syntheses of heteroaryloxiranes
    Troisi, L
    De Vitis, L
    Granito, C
    Metrangolo, P
    Pilati, T
    Ronzini, L
    ARKIVOC, 2004, : 61 - 73
  • [29] Formal enantioselective syntheses of oseltamivir and tamiphosphor
    Silva, Saul
    Maycock, Christopher D.
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 236 - 240
  • [30] Pyrinap ligands for enantioselective syntheses of amines
    Qi Liu
    Haibo Xu
    Yuling Li
    Yuan Yao
    Xue Zhang
    Yinlong Guo
    Shengming Ma
    Nature Communications, 12
12345