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A stereospecific pathway for the introduction of deuterium or tritium on the brassinosteroid skeleton by reductive dechlorination of chlorocarbonates
- 1.0388291 - ÚOCHB 2013 DE eng A - Abstract
Marek, Aleš - Patil, Mahadeo Rajshekhar - Klepetářová, Blanka - Kohout, Ladislav - Elbert, Tomáš
A stereospecific pathway for the introduction of deuterium or tritium on the brassinosteroid skeleton by reductive dechlorination of chlorocarbonates.
11th International Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds. Heidelberg: -, 2012. s. 55-55.
[International Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds /11./. 09.09.2012-13.09.2012, Heidelberg]
R&D Projects: GA AV ČR IAA400550801
Institutional research plan: CEZ:AV0Z40550506
Keywords : brassinosteroids * reductive dechlorination * tritium
Subject RIV: CC - Organic Chemistry
A new and efficient procedure for the preparation of brassinosteroids labeled with hydrogen isotopes was developed. A four-step reaction sequence started with the selective oxidation of a 2,3-diol group to an alfa-hydroxy ketone, which was converted stereospecifically into a chlorocarbonate by reaction with triphosgene. A subsequent Pd-catalyzed reductive dechlorination with deuterium or tritium gas yielded labeled brassinosteroid 2,3-carbonates. The reaction sequence was completed by base-catalyzed hydrolysis of the cyclic carbonate.
Permanent Link: http://hdl.handle.net/11104/0217278
Number of the records: 1