Regio- and stereoselective C-H functionalization of brassinosteroids

Alaksiej L Hurski; Aliaksandr G Kukel; Aliaksandra I Liubina; Aliona G Baradzenka; Darya Straltsova; Vadim Demidchik; Pavel Drašar; Vladimir N Zhabinskii; Vladimir A Khripach

doi:10.1016/j.steroids.2019.03.010

Regio- and stereoselective C-H functionalization of brassinosteroids

Steroids. 2019 Jun:146:92-98. doi: 10.1016/j.steroids.2019.03.010. Epub 2019 Apr 2.

Authors

Alaksiej L Hurski¹, Aliaksandr G Kukel², Aliaksandra I Liubina², Aliona G Baradzenka², Darya Straltsova³, Vadim Demidchik³, Pavel Drašar⁴, Vladimir N Zhabinskii², Vladimir A Khripach²

Affiliations

¹ Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich St., 5/2, 220141 Minsk, Belarus. Electronic address: AHurski@iboch.by.
² Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich St., 5/2, 220141 Minsk, Belarus.
³ Department of Plant Cell Biology and Bioengineering, Biological Faculty, Belarusian State University, Minsk, Belarus.
⁴ University of Chemistry and Technology, Technická 5, CZ-166 28 Praha 6, Czech Republic.

PMID: 30951761
DOI: 10.1016/j.steroids.2019.03.010

Abstract

Late stage CH functionalization is a powerful tool for modification of natural compounds. Herein we report that the rhodium-catalyzed reaction of brassinosteroids with aryloxysulfonamides proceeds regio- and stereoselectively at C15 position. The derivative obtained from 24-epibrassinolide was easily transformed to the conjugate with a BODIPY dye bearing unaffected functional groups of the native brassinosteroid.

Keywords: BODIPY; Brassinosteroids; C–H amination.

Publication types

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

MeSH terms

Boron Compounds / chemistry
Brassinosteroids / chemistry*
Catalysis
Rhodium / chemistry
Stereoisomerism

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
Brassinosteroids
Rhodium