Studies on the reactivity of 23E-benzylidene spirostanes

[Display omitted] •Catalytic hydrogenation of 23E-benzylidene spirostanes led to benzyl spirostanes.•Epoxidation of 23E-benzylidene spirostanes led to 23,23′-epoxybenzyl spirostanes.•Lewis acid catalyzed rearrangement led to spiro[furan]indenes.•Bronsted acid catalyzed rearrangement led to benzylide...

Full description

Saved in:
Bibliographic Details
Published in:Steroids 2019-11, Vol.151, p.108462-108462, Article 108462
Main Authors: Ramos-Enríquez, Manuel A., Flores-Álamo, Marcos, Iglesias-Arteaga, Martín A.
Format: Article
Language:English
Subjects:
Acid catalyzed rearrangements
Benzylidene Compounds - chemistry
Benzylidene spirostanes
Catalysis
Catalytic hydrogenation
Epoxidation
Hydrogenation
Models, Molecular
Molecular Conformation
NMR
Spirostans - chemistry
X-ray Diffraction
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] •Catalytic hydrogenation of 23E-benzylidene spirostanes led to benzyl spirostanes.•Epoxidation of 23E-benzylidene spirostanes led to 23,23′-epoxybenzyl spirostanes.•Lewis acid catalyzed rearrangement led to spiro[furan]indenes.•Bronsted acid catalyzed rearrangement led to benzylidene furostenes. A study of the reactivity of 25R and 25S 23E-benzylidene spirostanes that includes epoxidation, catalytic hydrogenation as well as Lewis or Brønsted acid-catalyzed rearrangements is described. Exhaustive NMR characterization of the obtained compounds is presented. Additionally the structures of some of the obtained compounds were confirmed by single crystal X-Ray Diffraction studies.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2019.108462