Synthesis of [26-2H3]-6-deoxo-24-epicastasterone

被引：4

作者：

Khripach, V. A. ^{[1
]}

Zhabinskii, V. N. ^{[1
]}

Gulyakevich, O. V. ^{[1
]}

Ermolovich, Yu. V. ^{[1
]}

机构：

[1] Natl Acad Sci Belarus, Inst Bioorgan Chem, Minsk 220141, BELARUS

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2012年 / 48卷 / 04期

关键词：

brassinosteroids; epibrassinolide; 6-deoxo-24-epicastasterone; deoxygenation; labeled compounds; BRASSINOSTEROIDS; BRASSINOLIDE; ANALOGS; CRINOSTEROL;

D O I：

10.1007/s10600-012-0322-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Deuterium-labeled 6-deoxo-24-epicastasterone was synthesized as a tool for studying the biosynthesis of 24-epibrassinolide in plants. The carbon skeleton of the side chain with the required C-24 methyl stereochemistry was constructed through a Claisen rearrangement. Deuterium atoms were introduced by reduction with LiAlD4 of the obtained gamma,delta-unsaturated ester. Both diols were introduced as a result of Sharpless asymmetric dihydroxylation of the intermediate a dagger(2,22)-diene.

引用

页码：601 / 605

页数：5

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