A facile method for steroid labeling by heavy isotopes of hydrogen

0446369 - ÚOCHB 2016 RIV GB eng J - Článek v odborném periodiku
Marek, Aleš - Klepetářová, Blanka - Elbert, Tomáš
A facile method for steroid labeling by heavy isotopes of hydrogen.
Tetrahedron. Roč. 71, č. 29 (2015), s. 4874-4882. ISSN 0040-4020. E-ISSN 1464-5416
Grant CEP: GA AV ČR IAA400550801
Institucionální podpora: RVO:61388963
Klíčová slova: brassinosteroids * alpha-hydroxy ketones * reductive dehalogenation * tritium * labeled compounds
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.645, rok: 2015

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).
Trvalý link: http://hdl.handle.net/11104/0248376