Synthesis of ergostane-type brassinosteroids with modifications in ring A

Herein, we present a new strategy for the preparation of a broad range of brassinosteroid biosynthetic precursors/metabolites differing by the ring A fragment. The protocol is based on the use of readily available phytohormones of this class bearing a 2α,3α-diol moiety (epibrassinolide or epicastast...

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Main Authors:	Vladimir N. Zhabinskii, Darya A. Osiyuk, Yuri V. Ermolovich, Natalia M. Chaschina, Tatsiana S. Dalidovich, Miroslav Strnad, Vladimir A. Khripach
Format:	Article
Language:	English
Published:	Beilstein-Institut 2017-11-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	biosynthetic precursors brassinosteroids diols epibrassinolide epicastasterone metabolites
Online Access:	https://doi.org/10.3762/bjoc.13.229

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spelling	doaj-75982e52778b4c8997ecea1dc11e82a02021-04-02T07:13:28ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-11-011312326233110.3762/bjoc.13.2291860-5397-13-229Synthesis of ergostane-type brassinosteroids with modifications in ring AVladimir N. Zhabinskii0Darya A. Osiyuk1Yuri V. Ermolovich2Natalia M. Chaschina3Tatsiana S. Dalidovich4Miroslav Strnad5Vladimir A. Khripach6Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich st., 5/2, 220141 Minsk, BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich st., 5/2, 220141 Minsk, BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich st., 5/2, 220141 Minsk, BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich st., 5/2, 220141 Minsk, BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich st., 5/2, 220141 Minsk, BelarusLaboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech RepublicInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich st., 5/2, 220141 Minsk, BelarusHerein, we present a new strategy for the preparation of a broad range of brassinosteroid biosynthetic precursors/metabolites differing by the ring A fragment. The protocol is based on the use of readily available phytohormones of this class bearing a 2α,3α-diol moiety (epibrassinolide or epicastasterone) as starting materials. The required functionalities (Δ2-, 2α,3α- and 2β,3β-epoxy-, 2α,3β-, 2β,3α-, and 2β,3β-dihydroxy-, 3-keto-, 3α- and 3β-hydroxy-, 2α-hydroxy-3-keto-) were synthesized from 2α,3α-diols in a few simple steps (Corey–Winter reaction, epoxidation, oxidation, hydride reduction, etc.).https://doi.org/10.3762/bjoc.13.229biosynthetic precursorsbrassinosteroidsdiolsepibrassinolideepicastasteronemetabolites
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Vladimir N. Zhabinskii Darya A. Osiyuk Yuri V. Ermolovich Natalia M. Chaschina Tatsiana S. Dalidovich Miroslav Strnad Vladimir A. Khripach
spellingShingle	Vladimir N. Zhabinskii Darya A. Osiyuk Yuri V. Ermolovich Natalia M. Chaschina Tatsiana S. Dalidovich Miroslav Strnad Vladimir A. Khripach Synthesis of ergostane-type brassinosteroids with modifications in ring A Beilstein Journal of Organic Chemistry biosynthetic precursors brassinosteroids diols epibrassinolide epicastasterone metabolites
author_facet	Vladimir N. Zhabinskii Darya A. Osiyuk Yuri V. Ermolovich Natalia M. Chaschina Tatsiana S. Dalidovich Miroslav Strnad Vladimir A. Khripach
author_sort	Vladimir N. Zhabinskii
title	Synthesis of ergostane-type brassinosteroids with modifications in ring A
title_short	Synthesis of ergostane-type brassinosteroids with modifications in ring A
title_full	Synthesis of ergostane-type brassinosteroids with modifications in ring A
title_fullStr	Synthesis of ergostane-type brassinosteroids with modifications in ring A
title_full_unstemmed	Synthesis of ergostane-type brassinosteroids with modifications in ring A
title_sort	synthesis of ergostane-type brassinosteroids with modifications in ring a
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2017-11-01
description	Herein, we present a new strategy for the preparation of a broad range of brassinosteroid biosynthetic precursors/metabolites differing by the ring A fragment. The protocol is based on the use of readily available phytohormones of this class bearing a 2α,3α-diol moiety (epibrassinolide or epicastasterone) as starting materials. The required functionalities (Δ2-, 2α,3α- and 2β,3β-epoxy-, 2α,3β-, 2β,3α-, and 2β,3β-dihydroxy-, 3-keto-, 3α- and 3β-hydroxy-, 2α-hydroxy-3-keto-) were synthesized from 2α,3α-diols in a few simple steps (Corey–Winter reaction, epoxidation, oxidation, hydride reduction, etc.).
topic	biosynthetic precursors brassinosteroids diols epibrassinolide epicastasterone metabolites
url	https://doi.org/10.3762/bjoc.13.229
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Synthesis of ergostane-type brassinosteroids with modifications in ring A

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