Skip to main content
SpringerLink
Log in

A new route to steroid ring C aromatization from readily available precursors

  • Symposium: Sterols Held at the AOCS Annual Meeting in New Orleans, LA, May 17–21, 1981
  • Published:
Lipids

Abstract

3β-Acetoxy-8α,9α-epoxy-5α-cholest-14-ene (1); 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-ene (2); 3β-acetoxy-5α-cholest-8(14)-ene-9α,15α-diol (3); and 3β-acetoxy-5α-cholesta-8(14),9(11)-dien-15α-ol (4) have been aromatized to a 9∶1 mixture of 3β-hydroxy-12-methyl-18-nor-5α,17β(H)-cholesta-8,11,13-triene (5a) and 3β-hydroxy-12-methyl-18-nor-5α,17α(H)-cholesta-8,11,13-triene (5b) in ethanol solution by using hydrochloric acid. The aromatization by action ofp-toluenesulfonic acid gave mainly the epimer with the natural C-17 configuration as the acetate 5c at the appropriatep-toluenesulfonic acid concentration. 3β-Acetoxy-5α-cholesta-7,9(11),14-triene (7a) and 3β-hydroxy-5α-cholesta-8,11,14-triene (8a), 2 intermediary compounds in the aromatization, were isolated and characterized.

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

Similar content being viewed by others

References

  1. Khanapure, S.P., Hazra, B.G., and Das, K.G. (1981) J. Chem. Soc. Perkin Trans. I, 1360–1362.

    Article  Google Scholar 

  2. Dalzell, H.C., Manmade, A., Mastrocola, A.R., and Razdan, R.K. (1979) J. Org. Chem. 44, 2457–2461.

    Article  CAS  Google Scholar 

  3. Anastasia, M., Allevi, P., Fiecchi, A., and Scala, A. (1981) J. Org. Chem. 46, 3265–3267.

    Article  CAS  Google Scholar 

  4. Still, W.C., Kahn, M., and Mitra, A. (1978) J. Org. Chem. 43, 2923–2925.

    Article  CAS  Google Scholar 

  5. Edmunds, R., Midgley, J.M., Tagg, L.G., Wilkins, B.J., and Whalley, W.B. (1978) J. Chem. Soc. Perkin Trans. I, 76–80.

    Article  Google Scholar 

  6. Anastasia, M., Fiecchi, A., and Scala, A. (1979) J. Chem. Soc. Perkin Trans. I, 1821–1824.

    Article  Google Scholar 

  7. Margulis, T.N., Hammer, C.F., and Stevenson, R. (1964) J. Chem. Soc. 4396–4400.

  8. Anastasia, M., Fiecchi, A., and Scala, A. (1978) J. Org. Chem. 43, 3505–3508.

    Article  CAS  Google Scholar 

  9. Aberhart, D.J., Cahn, T.Y., and Caspi, E. (1979) J. Chem. Soc. Perkin Trans. I, 220–224.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, School of Medicine, University of Milan, Via Saldini 50, I-20133, Italy

    Mario Anastasia, Pietro Allevi, Alberto Fiecchi & Antonio Scala

Authors
  1. Mario Anastasia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pietro Allevi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alberto Fiecchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Antonio Scala
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Anastasia, M., Allevi, P., Fiecchi, A. et al. A new route to steroid ring C aromatization from readily available precursors. Lipids 17, 226–229 (1982). https://doi.org/10.1007/BF02535108

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02535108

Keywords

Search

Navigation