Literature DB >> 19463690

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

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

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.

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Year:  2009        PMID: 19463690     DOI: 10.1016/j.steroids.2009.02.010

Source DB:  PubMed          Journal:  Steroids        ISSN: 0039-128X            Impact factor:   2.668


  1 in total

1.  A Convenient Synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam and its N-alkyl Derivatives.

Authors:  Agnieszka Wojtkielewicz; Damian Pawelski; Przemysław Bazydło; Aneta Baj; Stanisław Witkowski; Jacek W Morzycki
Journal:  Molecules       Date:  2020-05-20       Impact factor: 4.411

  1 in total

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