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

Irina D Alshakova; Yuri V Ermolovich; Vladimir N Zhabinskii; Vladimir A Khripach

doi:10.1016/j.steroids.2014.08.020

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

Steroids. 2015 May:97:72-7. doi: 10.1016/j.steroids.2014.08.020. Epub 2014 Sep 3.

Authors

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

Affiliations

¹ Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk, Belarus.
² Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk, Belarus. Electronic address: [email protected].

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

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.

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

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Brassinosteroids / chemical synthesis*
Brassinosteroids / chemistry
Cholestanes / chemistry*
Molecular Conformation
Stereoisomerism

Substances

Brassinosteroids
Cholestanes