Skip to main content
SpringerLink
Log in

Unusual oxidation reactions of 7α-methyl- and 7α-phenylcholest-5-ene-3β,7β-diol

Ungewöhnliche Oxidation von 7α-Methyl- und 7α-Phenylcholest-3-en-3β,7β-diol

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Ozonation of 7α-methyl (or 7α-phenyl) cholest-5-ene-3β,7β-diol 3-TBDMS ether afforded the corresponding 5β,6β-epoxy derivatives. The same product was formed byMCPBA oxidation. The reaction of 7α-phenylcholest-5-ene-3β,7β-diol with CrO3 yielded 3,7-dioxo-6,7-seco-7-phenylcholest-4-ene-5-carboxaldehyde. An analogous B-seco aldehyde was obtained from 7α-methylcholest-5-ene-3β,7β-diol in addition to 7-methylcholesta-4,6-dien-3-one.Jones oxidation of 7α-phenylcholest-5-ene-3β,7β-diol or B-seco-aldehyde gave 3,7-dioxo-6,7-seco-7-phenylcholest-4-en-6-oic acid isolated as its methyl ester upon treatment with diazomethane.

Zusammenfassung

Ozonolyse von 7α-Methyl- bzw. 7α-Phenyl-cholest-3-en-3β,7β-diol-3-TBDMS-ether ergab die entsprechenden 5β,6β-Epoxy-Derivate.MCPBA-Oxidation führte zum gleichen Ergebnis. Bei der Reaktion von 7α-Phenyl-cholest-5-en-3β,7β-diol mit CrO3 wurde 3,7-Dioxo-6,7-seco-7-phenyl-cholest-4-en-5-carbaldehyd gebildet. Einen analogen B-seco-Aldehyd erhält man neben 7-Methyl-cholesta-4,6-dien-3-on auch aus 7α-Methyl-cholest-5-en-3β,7β-diol. DurchJones-Oxidation von 7α-Phenyl-cholest-5-en-3β,7β-diol oder B-seco-Aldehyd erhält man 3,7-Dioxo-6,7-seco-7-phenylcholest-4-en-6-carbonsäure, die nach Behandlung mit Diazomethan als ihr Methylester isoliert wurde.

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. Geller J (1991) J Am Geriatr Soc39: 1208

    Google Scholar 

  2. Frye SV, Haffner CD, Maloney PR, Mook RA Jr, Dorsey GF Jr, Hiner RN, Cribbs CM, Wheeler TN, Ray JA, Andrews RC, Batchelor KW, Bramson HN, Stuart JD, Schweiker SL, van Arnold J, Croom S, Bickett DM, Moss ML, Tian G, Unwalla RJ, Lee FW, Tippin TK, James MK, Grizzle MK, Long JE, Schuster SV (1994) J Med Chem37: 2352

    Google Scholar 

  3. Russell DW, Wilson JD (1994) Ann Rev Biochem63: 25

    Google Scholar 

  4. Bakshi RK, Patel GF, Rasmusson GH, Baginsky WF, Cimis G, Ellsworth K, Chang B, Bull H, Tolman RL, Harris GS (1994) J Med Chem37: 3871

    Google Scholar 

  5. Haffner C (1995) Tetrahedron Lett36: 4039

    Google Scholar 

  6. Kasal A (1983) Coll Czech Chem Comm48: 1489

    Google Scholar 

  7. Bann B, Heilbron IM, Spring FS (1936) J Chem Soc: 1274

  8. Weinhouse S, Kharasch MS (1936) J Org Chem 1: 490

    Google Scholar 

  9. Baldwin J (1976) J Chem Soc, Chem Comm: 738

  10. Bailey PS, Lane AG (1967) J Am Chem Soc89: 4473

    Google Scholar 

  11. House HO (1972) Modern synthetic reactions, 2nd edn. The Benjamin/Cummings Publ. Comp., Menlo Park, California, USA, Chapt 6, pp 303–305 and references therein

    Google Scholar 

  12. Campbell JA, Babcock JC (1959) J Am Chem Soc81: 4069

    Google Scholar 

  13. Robinson CH, Gnoj O, Charney W, Gilmore ML, Oliveto EP (1959) J Am Chem Soc81: 408

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, University of Warsaw, Bialystok Branch, PL-15443, Bialystok, Poland

    J. W. Morzycki, Z. Dąbrowski, M. Trusewicz & A. Z. Wilczewska

Authors
  1. J. W. Morzycki
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Z. Dąbrowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Trusewicz
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. Z. Wilczewska
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Morzycki, J.W., Dąbrowski, Z., Trusewicz, M. et al. Unusual oxidation reactions of 7α-methyl- and 7α-phenylcholest-5-ene-3β,7β-diol. Monatsh Chem 127, 1283–1289 (1996). https://doi.org/10.1007/BF00807796

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807796

Keywords

Search

Navigation