Synthesis of ergostane-type brassinosteroids with modifications in ring A

被引：2

作者：

Zhabinskii, Vladimir N. ^{[1
]}

Osiyuk, Darya A. ^{[1
]}

Ermolovich, Yuri V. ^{[1
]}

Chaschina, Natalia M. ^{[1
]}

Dalidovich, Tatsiana S. ^{[1
]}

Strnad, Miroslav ^{[2
,3
]}

Khripach, Vladimir A. ^{[1
]}

机构：

[1] Natl Acad Sci Belarus, Inst Bioorgan Chem, Kuprevich St 5-2, Minsk 220141, BELARUS

[2] Inst Expt Bot ASCR, Ctr Reg Hana Biotechnol & Agr Res, Lab Growth Regulators, Slechtitelu 27, CZ-78371 Olomouc, Czech Republic

[3] Palacky Univ, Slechtitelu 27, CZ-78371 Olomouc, Czech Republic

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷

基金：

俄罗斯科学基金会;

关键词：

biosynthetic precursors; brassinosteroids; diols; epibrassinolide; epicastasterone; metabolites; BIOSYNTHETIC PRECURSORS; BRASSINOLIDE; 24-EPI-CASTASTERONE; METABOLITES; DERIVATIVES; TOXICITY;

D O I：

10.3762/bjoc.13.229

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.).

引用

页码：2326 / 2331

页数：6

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