Concise total synthesis of (±)-aspidospermidine via an oxidative Hosomi-Sakurai process

被引:70
|
作者
Sabot, Cyrille [1 ]
Guerard, Kimiaka C. [1 ]
Canesi, Sylvain [1 ]
机构
[1] Univ Quebec, Lab Methodol & Synth Prod Nat, Montreal, PQ H3C 3P8, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
FORMAL 2+3 CYCLOADDITION; HYPERVALENT IODINE(III) REAGENT; BIARYL COUPLING REACTION; ASPIDOSPERMA ALKALOIDS; INDOLE ALKALOIDS; ENANTIOSPECIFIC SYNTHESIS; SUBSTITUTED PHENOLS; TRICYCLIC AMINES; RECENT PROGRESS; DERIVATIVES;
D O I
10.1039/b903530c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise total synthesis of (+/-)-aspidospermidine has been achieved in twelve steps from inexpensive 4-ethylphenol, based on an oxidative Hosomi-Sakurai reaction via the concept of "aromatic ring umpolung".
引用
收藏
页码:2941 / 2943
页数:3
相关论文
共 50 条
  • [1] On the Way to an Oxidative Hosomi-Sakurai Reaction
    Sabot, Cyrille
    Commare, Bruno
    Duceppe, Marc-Alexandre
    Nahi, Salima
    Guerard, Kimiaka C.
    Canesi, Sylvain
    SYNLETT, 2008, (20) : 3226 - 3230
  • [2] Use of the Hosomi-Sakurai allylation in natural product total synthesis
    Lee, Jun Hee
    TETRAHEDRON, 2020, 76 (33)
  • [3] Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction
    Wilkie, Ross. P.
    Neal, Andrew R.
    Johnston, Craig A.
    Voute, Nicholas
    Lancefield, Christopher S.
    Stell, Matthew D.
    Medda, Federico
    Makiyi, Edward F.
    Turner, Emma M.
    Ojo, O. Stephen
    Slawin, Alexandra M. Z.
    Lebl, Tomas
    Mullen, Peter
    Harrison, David J.
    Ireland, Chris M.
    Westwood, Nicholas J.
    CHEMICAL COMMUNICATIONS, 2016, 52 (71) : 10747 - 10750
  • [4] An oxidative Hosomi-Sakurai strategy toward the synthesis of illioliganones B and C
    Moran, Wesley J.
    Rodriguez, Arantxa
    RSC ADVANCES, 2011, 1 (01) : 33 - 35
  • [5] Gold-catalyzed Hosomi-Sakurai type reaction for the total synthesis of herboxidiene
    Thirupathi, Barla
    Mohapatra, Debendra K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (26) : 6212 - 6224
  • [6] Intramolecular Hosomi-Sakurai Reaction for the Synthesis of Benzoxasiloles
    Yu, Xin-Long
    Hu, Jia-Wei
    Cao, Jian
    Xu, Li-Wen
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 9027 - 9030
  • [7] Total Synthesis of Natural Enantiomers of Heliespirones A and C via the Diastereoselective Intramolecular Hosomi-Sakurai Reaction
    Miyawaki, Akari
    Kikuchi, Daisuke
    Niki, Masu
    Manabe, Yuki
    Kanematsu, Makoto
    Yokoe, Hiromasa
    Yoshida, Masahiro
    Shishido, Kozo
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18): : 8231 - 8243
  • [8] Functionalisation of isoindolinones via a calcium catalysed Hosomi-Sakurai allylation
    Basson, Ashley J.
    McLaughlin, Mark G.
    CHEMICAL COMMUNICATIONS, 2019, 55 (57) : 8317 - 8320
  • [9] Synthesis of Homoallylamine Covalent Organic Frameworks Via Hosomi-Sakurai Reaction Under Mild Conditions
    Zorigt, Naranchimeg
    Zarei, Amin
    Auras, Florian
    Khazdooz, Leila
    Khosropour, Ahmadreza
    Abbaspourrad, Alireza
    SMALL, 2024,
  • [10] Concise total synthesis of (±)-aspidospermidine
    Ma, Haichen
    Xie, Xingang
    Jing, Peng
    Zhang, Weiwei
    She, Xuegong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (18) : 5255 - 5259