Short Access to the Aromadendrane Family: Highly Efficient Stereocontrolled Total Synthesis of (±)-Cyclocolorenone and (±)-α-Gurjunene

被引：7
|
作者：
Calancea, Mihaela [1 ]
Carret, Sebastien [1 ]
Depres, Jean-Pierre [1 ]
机构：
[1] CNRS, ICMG FR 2607, SERCO UMR 5250, Dept Chim Mol, F-38041 Grenoble 9, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 19期
关键词：
Total synthesis; Sesquiterpenes; Isomerization; Hydrogenation; Cyclopropanation; CYCLOCOLORENONE; SESQUITERPENES; DERIVATIVES; REDUCTION; HYDROGENATION; GURJUNENE; ETHYLENE; OLEFINS; SYSTEMS; KETONES;
D O I：
10.1002/ejoc.200900253
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(+/-)-Cyclocolorenone (2), an aromadendrane, was prepared stereoselectively in seven steps in 10.8-12.5% overall yield from the commercially available tropylium cation via key intermediate 6, which was used as a general and efficient precursor to bicyclo[5.3.0]decane sesquiterpenes. (+/-)-alpha-Gurjunene (3) was obtained through the efficient deoxygenation of (+/-)-2, constituting therefore the first total synthesis of this natural product in eight steps from the tropylium cation. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码：3134 / 3137
页数：4
相关论文
共 28 条
  • [1] Highly efficient stereocontrolled total synthesis of (+)-upial
    Takahashi, Kazunori
    Watanabe, Masayuki
    Honda, Toshio
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 131 - 133
  • [2] Highly efficient stereocontrolled total synthesis of the polyfunctional carotenoid peridinin
    Furuichi, N
    Hara, H
    Osaki, T
    Mori, H
    Katsumura, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (06) : 1023 - +
  • [3] A Short and Efficient Total Synthesis of Ficuseptamines A and B
    Hassan, Hani Mutlak A.
    MOLECULES, 2018, 23 (08)
  • [4] A highly stereocontrolled asymmetric total synthesis of epimer of (+)-7-deoxypancratistatin
    Chavan, Subhash P.
    Garai, Sumanta
    Dey, Chandan
    Gonnade, Rajesh G.
    TETRAHEDRON LETTERS, 2013, 54 (41) : 5562 - 5566
  • [5] Highly efficient total synthesis of (+)-citreoviral
    Murata, Y
    Kamino, T
    Aoki, T
    Hosokawa, S
    Kobayashi, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (24) : 3175 - 3177
  • [6] A highly efficient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-DMT]
    Balducci, Daniele
    Contaldi, Simone
    Lazzari, Ilaria
    Porzi, Gianni
    TETRAHEDRON-ASYMMETRY, 2009, 20 (12) : 1398 - 1401
  • [7] Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes
    Yuan, Changxia
    Jin, Yehua
    Wilde, Nathan C.
    Baran, Phil S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (29) : 8280 - 8284
  • [8] Highly efficient and stereocontrolled oxidative coupling of tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and (+)-WIN 64745
    Sun, Deqian
    Xing, Changyu
    Wang, Xiaoqing
    Su, Zhongquan
    Li, Chaozhong
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (08): : 956 - 960
  • [9] Stereocontrolled addition of Grignard reagents to oxa-bridged benzazepines: highly efficient synthesis of functionalized benzazepine scaffolds
    Zhang, Yuewei
    Bao, Qingqing
    Zhang, Ning
    Wang, Shuohang
    Yu, Xue
    RSC ADVANCES, 2020, 10 (68) : 41802 - 41806
  • [10] An Efficient and Short Total Synthesis of (-)-Heliannuol A by Intramolecular Ullmann C-O Coupling for the Construction of an Eight-Membered Ether Ring
    Tsubogo, Tetsu
    Okamura, Fumiya
    Omori, Akiho
    Uchiro, Hiromi
    CHEMISTRYSELECT, 2021, 6 (17): : 4224 - 4228
123