4.4 Article

A stereospecific pathway for the introduction of deuterium on the brassinosteroid skeleton by reductive dechlorination of chlorocarbonates

期刊

TETRAHEDRON LETTERS
卷 53, 期 16, 页码 2048-2050

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.02.013

关键词

Reductive dechlorination; Stereospecific reactions; Labeled compounds; Brassinosteroids; Chlorocarbonates

资金

  1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic [Z40550506]
  2. Grant Agency of the Academy of Sciences of the Czech Republic [IAA400550801]

向作者/读者索取更多资源

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 alpha-hydroxy ketone, which was converted stereospecifically into a chlorocarbonate by reaction with triphosgene. A subsequent Pd-catalyzed reductive dechlorination with deuterium gas yielded deuterium-labeled brassinosteroid 2,3-carbonates. The reaction sequence was completed by base-catalyzed hydrolysis of the cyclic carbonate. (C) 2012 Elsevier Ltd. All rights reserved.

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