Skip to main content
Log in

An improved and efficient synthesis for IPL576,092 and its analogues

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

Abstract

An improved and efficient preparation of IPL576,092 was developed. The synthetic route involves selective allylic oxidation of ∆5-sterols and subsequent hydroboration–oxidation as the key steps. In addition, two analogues were readily synthesized from commercially available steroidal compounds in two steps in the same way.

Graphical abstract

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Burgoyne DL, Andersen RJ (1992) J Org Chem 57:525

    Article  CAS  Google Scholar 

  2. Shen Y, Burgoyne DL (2002) J Org Chem 67:3908

    Article  CAS  Google Scholar 

  3. Izzo I, Avallone E, Monica CD, Casapullo A, Amigo M, Riccardis FD (2004) Tetrahedron 60:5587

    Article  CAS  Google Scholar 

  4. Kasserra CE, Harris P, Stenton GR, Abraham W, Langlands JM (2004) Pulm Pharmacol Ther 17:309

    Article  CAS  Google Scholar 

  5. Filippo MD, Izzo I, Savignano L, Tecilla P, Riccardis FD (2003) Tetrahedron 59:1711

    Article  Google Scholar 

  6. Burgoyne DL, Shen Y, Langlands JM, Rogers C, Chau JH-L, Piers E, Salari H (2004) Preparation of 6,7-oxygenated steroids and uses related thereto. US Patent 6,706,701, 16 Mar 2004

  7. Liu J, Zhu HY, Cheng XH (2009) Synth Commun 39:1076

    Article  CAS  Google Scholar 

  8. Foricher J, Furbringer C, Pfoertner K (1991) Process for the catalytic oxidation of isoprenoids having allylic groups. US Patent 5,030,739, 9 Jul 1991

  9. Huang M, Chen Z, Zhou W (1965) Acta Chim Sin 31:165

    CAS  Google Scholar 

Download references

Acknowledgments

Thanks are due to Prof Fu-Chu Liu (Yunnan University) for helpful criticism of the manuscript. This work was supported by the National Natural Science Foundation of China (No. 20472070) and State University College of Innovative Experimental Projects (No. 101067319).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jin Liu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, J., Huang, R. & Zhu, H. An improved and efficient synthesis for IPL576,092 and its analogues. Monatsh Chem 144, 1081–1085 (2013). https://doi.org/10.1007/s00706-012-0920-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0920-4

Keywords

Navigation