Download PDF
Synthesis 2023; 55(02): 289-296
DOI: 10.1055/a-1878-8597
paper
Special Issue dedicated to Prof. Alain Krief

A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

Yang Chen
a   Yunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China
,
Xin-Ting Hu
a   Yunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China
,
Xiao-Yan Xie
a   Yunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China
,
Dashan Li
a   Yunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China
,
Chun-Xia Zheng
a   Yunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China
,
You-Xi Zhang
b   School of Chemistry and Chemical Engineering, Yunnan Normal University, 798 Jvxian Street, Kunming, 650500, P. R. of China
,
Wen-Jing Wang
a   Yunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China
,
Rui Zhan∗
b   School of Chemistry and Chemical Engineering, Yunnan Normal University, 798 Jvxian Street, Kunming, 650500, P. R. of China
,
Li-Dong Shao  ∗
a   Yunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China
› Author AffiliationsThe authors gratefully acknowledge financial support from the National­ Natural Science of Foundation of China (81960631), the Yunnan­ Fundamental Research Project (202001AS070038), the Ten Thousand Talent Plans for Young Top-Notch Talents of Yunnan Province (R.Z. and L.-D.S.), and the Start-up Fund of Yunnan University of Chinese Medicine (2019YZG03).
› Further Information
    Permissions and Reprints All articles of this category


Abstract

We represented herein a two-step synthesis of 1-methyl-6H-indol-6-one which is an N-containing 6/5 fused bicyclic building blocks in Amaryllidaceae alkaloids. The key step featured is a ‘one-pot’ ozonolysis/reductive amination/cyclization of allylated cyclohexa-1,3-dione to give bicyclic compounds. Moreover, the formal total synthesis of natural product γ-lycorane could be achieved through a photo-promoted cyclization/oxidation cascade reaction from the resulting bicyclic intermediate.

Key words

1-methyl-6H-indol-6-one - two-step synthesis - one-pot - Amaryllidaceae alkaloids - γ-lycorane

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1878-8597.
  • Supporting Information


Publication History

Received: 27 May 2022

Accepted after revision: 20 June 2022

Accepted Manuscript online:
20 June 2022

Article published online:
11 August 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Červinka O. Collect. Czech. Chem. Commun. 1960; 25: 1183
    Crossref
    • 2a Wang L.-N, Cui Q, Yu Z.-X. J. Org. Chem. 2016; 81: 10165
      CrossrefPubMed
    • 2b Yang D.-Q, Chen Z.-R, Chen D.-Z, Hao X.-J, Li S.-L. Nat. Prod. Bioprospect. 2018; 8: 189
      CrossrefPubMed

      For selected reviews of Amaryllidaceae alkaloids syntheses, see:
    • 4a Jin Z. Nat. Prod. Rep. 2013; 30: 849
      CrossrefPubMed
    • 4b Jin Z. Nat. Prod. Rep. 2016; 33: 1318
      CrossrefPubMed
    • 4c Jin Z, Yao G. Nat. Prod. Rep. 2019; 36: 1462
      CrossrefPubMed

      • For selected recent total syntheses of lycorine alkaloids, see:
    • 4d Liang L, Li J, Shen B, Zhang Y, Liu J, Chen J, Liu D. Org. Biomol. Chem. 2021; 19: 2767
      CrossrefPubMed
    • 4e Sun Z, Zhou M, Li X, Meng X, Peng F, Zhang H, Shao Z. Chem. Eur. J. 2014; 20: 6112
      CrossrefPubMed
    • 4f Meng X.-L, Liu T, Sun Z.-W, Wang J.-C, Peng F.-Z, Shao Z.-H. Org. Lett. 2014; 16: 3044
      CrossrefPubMed
    • 4g Andreev IA, Ratmanova NK, Novoselov AM, Belov DS, Seregina IF, Kurkin AV. Chem. Eur. J. 2016; 22: 7262
      CrossrefPubMed
    • 4h Hall CJ. J, Marriott IS, Christensen KE, Day AJ, Goundry WR. F, Donohoe TJ. Chem. Commun. 2022; 58: 4966
      CrossrefPubMed
    • 4i Zhang T.-Y, Zhang L.-Y, Liang X, Wei K, Yang Y.-R. Org. Lett. 2022; 24: 2905
      CrossrefPubMed
  • 5 McLeod MC, Singh G, Plampin JN, Rane D, Wang JL, Day VW, Aubé J. Nat. Chem. 2014; 6: 133
    CrossrefPubMed
  • 6 Bryson TA, Gammill RB. Tetrahedron Lett. 1974; 15: 3963
    CrossrefPubMed
  • 7 Iida H, Takarai T, Kibayashi C. J. Org. Chem. 1978; 43: 975
    CrossrefPubMed
  • 8 Michael JP, Zwane MI. Tetrahedron Lett. 1992; 33: 4755
    CrossrefPubMed
    • 9a Shaw MH, Melikhova EY, Kloer DP, Whittingham WG, Bower JF. J. Am. Chem. Soc. 2013; 135: 4992
      CrossrefPubMed
    • 9b Shaw MH, Whittingham WG, Bower JF. Tetrahedron 2016; 72: 2731
      Crossref
  • 10 Zhang W, Pugh G. Tetrahedron 2003; 59: 4237
    CrossrefPubMed
  • 11 Chen YL, Mariano PS, Little GM, O’Brien D, Huesmann PL. J. Org. Chem. 1981; 46: 4643
    CrossrefPubMed
  • 12 Chen X, Martinez JS, Mohr JT. Org. Lett. 2015; 17: 378
    CrossrefPubMed
    • 13a Zhao Y, Zhou Y, Liang L, Yang X, Du F, Li L, Zhang H. Org. Lett. 2009; 11: 555
      CrossrefPubMed
    • 13b Johnson T, Pultar F, Menke F, Lautens M. Org. Lett. 2016; 18: 6488
      CrossrefPubMed
  • 14 Wang W, Dai J, Yang Q, Deng Y.-H, Peng F, Shao Z. Org. Lett. 2021; 23: 920
    CrossrefPubMed
  • 15 Iida H, Yuasa Y, Kibayashi C. J. Am. Chem. Soc. 1978; 100: 3598
    CrossrefPubMed
  • 16 Iida H, Aoyagi S, Kibayashi C. J. Chem. Soc., Perkin Trans. 1 1975; 2502
    CrossrefPubMed
  • 17 Tiner-Harding T, Mariano PS. J. Org. Chem. 1982; 47: 482
    Crossref
  • 18 Iida H, Yuasa Y, Kibayashi C. J. Org. Chem. 1979; 44: 1074
    Crossref
  • 19 Szymor-Pietrzak D, Khan MN, Pagès A, Kumar A, Depner N, Clive DL. J. J. Org. Chem. 2021; 86: 619
    CrossrefPubMed