Formal total synthesis of (±)-strictamine - the [2,3]-Stevens rearrangement for construction of octahydro-2H-2,8-methanoquinolizines

被引:38
|
作者
Eckermann, Ruben [1 ]
Breunig, Michael [1 ]
Gaich, Tanja [1 ]
机构
[1] Univ Konstanz, Dept Chem, Univ Str 10, D-78457 Constance, Germany
关键词
PICRALIMA-NITIDA SEEDS; AKUAMMILINE ALKALOIDS; (+/-)-ASPIDOPHYLLINE; (+)-SCHOLARISINE; KLAINEANA;
D O I
10.1039/c6cc06125g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
For decades, akuammiline alkaloids have attracted synthetic chemists due to their intriguing molecular architecture. Among the different structural elements embedded in their carboskeleton, the methano-quinolizidine system constitutes the signature structural element of this alkaloid family. Herein, we describe a novel synthetic access to this system which relies on a [2,3]-Stevens rearrangement and results in the formal synthesis of strictamine.
引用
收藏
页码:11363 / 11365
页数:3
相关论文
共 50 条
  • [1] Formal Total Synthesis of (±)-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements
    Eckermann, Ruben
    Breunig, Michael
    Gaich, Tanja
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (16) : 3938 - 3949
  • [2] The Aryne [2,3] Stevens Rearrangement
    Roy, Tony
    Thangaraj, Manikandan
    Kaicharla, Trinadh
    Kamath, Rupa V.
    Gonnade, Rajesh G.
    Biju, Akkattu T.
    ORGANIC LETTERS, 2016, 18 (20) : 5428 - 5431
  • [3] Applications of the [2,3]-Wittig rearrangement to total synthesis
    McGowan, G
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2002, 55 (12) : 799 - 799
  • [4] Studies on the [2,3]-Stevens rearrangement of aziridinium ions
    Rowlands, GJ
    Barnes, WK
    TETRAHEDRON LETTERS, 2004, 45 (28) : 5347 - 5350
  • [5] Synthesis of Functionalized β-Keto Arylthioethers by the Aryne Induced [2,3] Stevens Rearrangement of Allylthioethers
    Thangaraj, Manikandan
    Gaykar, Rahul N.
    Roy, Tony
    Biju, Akkattu T.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08): : 4470 - 4476
  • [6] Synthesis of (±)-Amathaspiramide F and Discovery of an Unusual Stereocontrolling Element for the [2,3]-Stevens Rearrangement
    Soheili, Arash
    Tambar, Uttam K.
    ORGANIC LETTERS, 2013, 15 (19) : 5138 - 5141
  • [7] ASYMMETRIC [2,3]-WITTIG REARRANGEMENT APPROACH TO THE FORMAL SYNTHESIS OF (+)-BREFELDIN-A
    TOMOOKA, K
    ISHIKAWA, K
    NAKAI, T
    SYNLETT, 1995, (09) : 901 - &
  • [8] Tandem cyclisation and [2,3]-Stevens rearrangement to 2-substituted pyrrolidines
    Smith, SC
    Bentley, PD
    TETRAHEDRON LETTERS, 2002, 43 (05) : 899 - 902
  • [9] Total Synthesis of Eupomatilones 1, 2, and 5 by Enantioselective [2,3]-Wittig Rearrangement
    Hirokawa, Yoshimi
    Kitamura, Maria
    Mizubayashi, Makoto
    Nakatsuka, Rie
    Kobori, Yuya
    Kato, Chiharu
    Kurata, Yuki
    Maezaki, Naoyoshi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (04) : 721 - 727
  • [10] Perfluorobutyl Iodide Mediated [1,2] and [2,3] Stevens Rearrangement for the Synthesis of Indolin-3-ones
    Chen, Zhen-Yu
    Lin, Bi-Zhen
    Chen, Lei
    Zou, Yong
    Yan, Ming
    Zhang, Xue-Jing
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (20) : 4368 - 4372