Erroneous epimerization at C-22 in sapogenins

Izabella Jastrzębska; Jacek W Morzycki

doi:10.1016/j.steroids.2015.04.001

Erroneous epimerization at C-22 in sapogenins

Steroids. 2015 Aug:100:17-20. doi: 10.1016/j.steroids.2015.04.001. Epub 2015 Apr 17.

Authors

Izabella Jastrzębska¹, Jacek W Morzycki²

Affiliations

¹ Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland.
² Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland. Electronic address: morzycki@uwb.edu.pl.

PMID: 25891092
DOI: 10.1016/j.steroids.2015.04.001

Abstract

A recent report [1] about the epimerization of steroidal sapogenins at C-22 by treatment with BF3 · OEt2 is incorrect. We proved that the epimerization of sapogenins with BF3 · OEt2 occurs at C-25 as in the case of other acid-catalyzed reactions previously studied.

Keywords: 22-epi-Sapogenins; Sapogenin isomerization; Sapogenins.

Publication types

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

MeSH terms

Boranes / chemistry
Catalysis
Diosgenin / chemistry
Sapogenins / chemistry*
Stereoisomerism

Substances

Boranes
Sapogenins
boron trifluoride
Diosgenin
yamogenin