Synthesis of ergostane-type brassinosteroids with modifications in ring A

0482095 - ÚEB 2018 RIV DE eng J - Journal Article
Zhabinskii, V.N. - Osiyuk, D.A. - Ermolovich, Y.V. - Chaschina, N.M. - Dalidovich, T.S. - Strnad, Miroslav - Khripach, V.A.
Synthesis of ergostane-type brassinosteroids with modifications in ring A.
Beilstein Journal of Organic Chemistry. Roč. 13, NOV 2 (2017), s. 2326-2331. ISSN 1860-5397. E-ISSN 1860-5397
R&D Projects: GA MŠMT(CZ) LO1204
Institutional support: RVO:61389030
Keywords : biosynthetic precursors * brassinosteroids * diols
OECD category: Organic chemistry
Impact factor: 2.330, year: 2017

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 2 alpha, 3 alpha-diol moiety (epibrassinolide or epicastasterone) as starting materials. The required functionalities (Delta(2)-, 2 alpha, 3 alpha- and 2 beta, 3 beta-epoxy-, 2 alpha, 3 beta-, 2 beta, 3 alpha-, and 2 beta, 3 beta-dihydroxy-, 3-keto-, 3a-and 3 beta-hydroxy-, 2 alpha-hydroxy-3-keto-) were synthesized from 2 alpha, 3 alpha-diols in a few simple steps (Corey-Winter reaction, epoxidation, oxidation, hydride reduction, etc.).
Permanent Link: http://hdl.handle.net/11104/0277513