Some observations on solasodine reactivity

Izabella Jastrzebska; Jacek W Morzycki

doi:10.1016/j.steroids.2017.08.015

Some observations on solasodine reactivity

Steroids. 2017 Nov:127:13-17. doi: 10.1016/j.steroids.2017.08.015. Epub 2017 Sep 5.

Authors

Izabella Jastrzebska¹, Jacek W Morzycki²

Affiliations

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

PMID: 28887171
DOI: 10.1016/j.steroids.2017.08.015

Abstract

This article presents new transformations of solasodine - a representative steroid alkaloid sapogenin from the Solanum family. Oxidation of N,O-diacetylated solasodine with either NaNO₂/BF_3·Et₂O or t-BuONO/BF_3·Et₂O resulted in partial degradation of the side chain to (20S)-3β-acetoxypregn-5-ene-20,16β-carbolactone (vespertilin acetate). The same starting compound when treated with TMSOTf afforded the corresponding pseudosapogenin after aqueous work-up. However, when the crude reaction mixture was directly subjected to purification on a silica gel column, efficient autoxidation to pregna-5,16-dien-3β-ol-20-one acetate was observed. One-step synthesis of this important drug intermediate from spirosolan alkaloids may be potentially exploited for large-scale production of steroid hormones.

Keywords: Alkaloids; Autoxidation; Sapogenins; Solasodine; Steroids.

Publication types

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

MeSH terms

Oxidation-Reduction
Solanaceous Alkaloids / chemistry*
Stereoisomerism

Substances

Solanaceous Alkaloids
solasodine