These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Regio- and stereocontrolled synthesis of novel steroidal isoxazolines: a new route to the formation of selectively modified steroid side chains.
    Author: Zhylitskaya H, Litvinovskaya R, Baranovsky A, Eigner V, Kratochvíl B, Drašar P, Khripach V.
    Journal: Steroids; 2013 Sep; 78(9):823-31. PubMed ID: 23664846.
    Abstract:
    1,3-Dipolar cycloaddition reaction of acetonitrile oxide to cis- and trans-22-hydroxy-24-alkoxycarbonyl-Δ(23)-steroids is investigated. An unusual stereochemical course of the cycloaddition, leading to the same set of the isoxazoline adducts for both (Z)- and (E)-disubstituted olefins is revealed. It is shown, the reaction is regioselective and all possible 4',5'-diastereoisomers of resulting isoxazolines can be prepared as major products by cycloaddition to the suitable alkene. The structure of the key compounds is confirmed by X-ray and 2D NMR analysis.
    [Abstract] [Full Text] [Related] [New Search]