Synthesis of novel hybrid steroid dimers by BF3·Et2O-catalyzed aldol condensation of 2-formyl-estradiol diacetate and steroid sapogenins

[Display omitted] •Aldol condensation of an estrogen and steroid sapogenin acetates led to steroid dimers.•Four new hybrid steroid dimers are described.•The estrogenic core is attached to the side chain of the steroid sapogenin. BF3·Et2O-catalyzed aldol condensation of steroid sapogenins with 2-form...

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Bibliographic Details
Published in:Steroids 2017-12, Vol.128, p.46-49
Main Authors: Ramos-Enríquez, Manuel A., Iglesias-Arteaga, Martín A.
Format: Article
Language:English
Subjects:
2-Formyl-estradiol diacetate
BF3·Et2O-catalyzed aldol condensation
NMR
Steroid dimers
Steroid sapogenins
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Summary:[Display omitted] •Aldol condensation of an estrogen and steroid sapogenin acetates led to steroid dimers.•Four new hybrid steroid dimers are described.•The estrogenic core is attached to the side chain of the steroid sapogenin. BF3·Et2O-catalyzed aldol condensation of steroid sapogenins with 2-formyl-estradiol diacetate afforded two novel classes of steroid dimers in which an estrogenic core is attached to the spirostanic side chain of an steroid sapogenin through an exocyclic double bond in position C-23, or through a spiro centre in C-22.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2017.10.008