Skip to main content
SpringerLink
Log in

An unexpected reaction of cinobufagin analogues in the presence of PPh3/I2

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

An unexpected reaction of cinobufagin analogues in the presence of PPh3/I2 in EtOAc at room temperature to obtain diene compounds has been described. The whole process is carried out under mild conditions and the desired products are formed in good yields. It provides a simple, effective, and novel reaction method for the synthesis of diene compounds from corresponding substrates.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Dasgupta A, Lopez AE, Wells A, Olsen M, Actor J (2001) Clin Chim Acta 309:91

    Article  CAS  Google Scholar 

  2. Chen KK, Kovarikove A (1967) J Pharm Sci 56:1535

    Article  CAS  Google Scholar 

  3. Lei M, Xiao Z, Ma B, Chen Y, Liu M, Liu J, Guo D, Liu X, Hu L (2016) Steroids 108:56

    Article  CAS  Google Scholar 

  4. Kawazoe N, Watabe M, Masuda Y (1999) Oncogene 18:2413

    Article  CAS  Google Scholar 

  5. Cao H, Shibayama-Imazu TY, Shinki T, Nakajo S, Nakaya K (2007) Anticancer Res 27:245

    CAS  Google Scholar 

  6. Das D, Anal JMH, Rokhum L (2016) J Chem Sci 128:1695

    Article  CAS  Google Scholar 

  7. Iseli E, Kotake M, Weiss E, Reichstein T (1963) Helv Chim Acta 48:1093

    Article  Google Scholar 

  8. Kamano Y, Yamamoto H, Hatayama K, Tanaka Y, Shinohara M, Komatsu M (1968) Tetrahedron Lett 54:5669

    Article  Google Scholar 

  9. Shimada K, Fujii Y, Yamashita E, Niizaki Y, Sato Y (1977) Chem Pharm Bull 25:714

    Article  CAS  Google Scholar 

  10. Verpoorte R, Svendsen AB (1980) J Nat Prod 43:347

    Article  CAS  Google Scholar 

  11. Nogawa T, Kamano Y, Yamashita A, Pettit GR (2001) J Nat Prod 64:1148

    Article  CAS  Google Scholar 

  12. Sun G, Lv X, Zhang Y, Lei M, Hu L (2017) Org Lett 19:4235

    Article  CAS  Google Scholar 

  13. Iranpoor N, Firouzabadi H, Chitsazi M, Jafari AA (2002) Tetrahedron 58:7037

    Article  CAS  Google Scholar 

  14. Zhou Y, Chen P, Lv X, Niu J, Wang Y, Lei M, Hu L (2017) Tetrahedron Lett 58:2232

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by Special Fund for Strategic Pilot Technology Chinese Academy of Sciences (XDA12020379), and the National Natural Science Foundation of China (Grants 81973455).

Author information

Authors and Affiliations

  1. Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People’s Republic of China

    Yang Zhou, Jinjun Hou, Huali Long, Zijia Zhang, Dean Guo, Min Lei & Wanying Wu

  2. University of Chinese Academy of Sciences, Beijing, 100049, People’s Republic of China

    Yang Zhou, Jinjun Hou, Huali Long, Zijia Zhang, Dean Guo, Min Lei & Wanying Wu

  3. College of Pharmacy, Dali University, Dali, 671000, People’s Republic of China

    Yanzhi Zhang & Xubing Chen

Authors
  1. Yang Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yanzhi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xubing Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jinjun Hou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Huali Long
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zijia Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Dean Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Min Lei
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Wanying Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Min Lei or Wanying Wu.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1177 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhou, Y., Zhang, Y., Chen, X. et al. An unexpected reaction of cinobufagin analogues in the presence of PPh3/I2. Monatsh Chem 151, 617–623 (2020). https://doi.org/10.1007/s00706-020-02577-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-020-02577-7

Keywords

Search

Navigation