A facile method for steroid labeling by heavy isotopes of hydrogen

被引：9

作者：

Marek, Ales ^{[1
]}

Klepetarova, Blanka ^{[1
]}

Elbert, Tomas ^{[1
]}

机构：

[1] Inst Organ Chem & Biochem ASCR, Vvi, Prague 16610 6, Czech Republic

来源：

TETRAHEDRON | 2015年 / 71卷 / 29期

关键词：

Brassinosteroids; alpha-Hydroxy ketones; Reductive dehalogenation; Tritium; Labeled compounds; BRASSINOSTEROIDS; CONVERSION; POSITION; ANALOGS; POLLEN;

D O I：

10.1016/j.tet.2015.04.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new catalytic enantiospecific approach to the synthesis of epibrassinosteroids (and other polyhydroxylated steroids) regiospecifically labeled by heavy isotopes of hydrogen is reported. Chlorocarbonate, efficiently synthesized from a-hydroxy ketone by a reaction with triphosgene, undergoes reductive tritium dechlorination catalyzed by the [Pd-0]/Et3N system, providing 24-[3 beta-H-3]epicastasterone and 24-[3 beta-H-3]epibrassinolide, respectively, in good yield and with high specific activity (5.8 Ci/mmol; 20% tritium enrichment per molecule). (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4874 / 4882

页数：9

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