Literature DB >> 25194458

A new synthesis of brassinosteroids with a cholestane framework based on a highly functionalized starting material.

Irina D Alshakova1, Yuri V Ermolovich1, Vladimir N Zhabinskii1, Vladimir A Khripach2.   

Abstract

A new route to the synthesis of minor brassinosteroids with a cholestane framework (28-norcastasterone and 28-norbrassinolide) has been proposed. It makes use of commercially available 24-epicastasterone as a starting material. In addition, [26,26,26-(2)H3]-28-norcastasterone and [26,26,26-(2)H3]-28-norbrassinolide have been prepared as tools for analytical applications. The key steps were regioselective manipulations of functional groups in 24-epicastasterone, oxidative cleavage of 22,23-diol group and Claisen rearrangement.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  24-Epicastasterone; 28-Norbrassinolide; Boric acid ester; Brassinosteroids; Claisen rearrangement; Deuterated analogues

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Substances:

Year:  2014        PMID: 25194458     DOI: 10.1016/j.steroids.2014.08.020

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


  1 in total

1.  Synthesis of ergostane-type brassinosteroids with modifications in ring A.

Authors:  Vladimir N Zhabinskii; Darya A Osiyuk; Yuri V Ermolovich; Natalia M Chaschina; Tatsiana S Dalidovich; Miroslav Strnad; Vladimir A Khripach
Journal:  Beilstein J Org Chem       Date:  2017-11-02       Impact factor: 2.883

  1 in total

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