On reactions of steroidal 23-oxo and 23,24-epoxysapogenins with Lewis acids

Izabella Jastrzebska; Leszek Siergiejczyk; Aneta M Tomkiel; Zofia Urbańczyk-Lipkowska; Dominik Wójcik; Jacek W Morzycki

doi:10.1016/j.steroids.2009.02.010

On reactions of steroidal 23-oxo and 23,24-epoxysapogenins with Lewis acids

Steroids. 2009 Aug;74(8):675-83. doi: 10.1016/j.steroids.2009.02.010. Epub 2009 Mar 14.

Authors

Izabella Jastrzebska¹, Leszek Siergiejczyk, Aneta M Tomkiel, Zofia Urbańczyk-Lipkowska, Dominik Wójcik, Jacek W Morzycki

Affiliation

¹ Institute of Chemistry, University of Białystok, Piłsudskiego 11/4, 15-443 Białystok, Poland.

PMID: 19463690
DOI: 10.1016/j.steroids.2009.02.010

Abstract

The reaction of 23-oxotigogenin acetate with TMSOTf in THF afforded the corresponding bisnorcholanic lactone in 60% yield. The analogous reactions carried out in dichloromethane or benzene gave the rearranged products--the isomeric spirostanic ketone (10-15%) and bisfuran (40-42%). Similar products were also obtained upon treatment of 23,24-epoxysapogenins with BF(3). The epoxides treated with TiCl(4) afforded mostly chlorohydrins and no rearranged products were detected.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Mesylates / chemistry
Sapogenins / chemistry*
Trimethylsilyl Compounds / chemistry

Substances

23-oxotigogenin acetate
Mesylates
Sapogenins
Trimethylsilyl Compounds
trimethylsilyl trifluoromethanesulfonate