Concise Synthesis of 23-Hydroxylated Vitamin D3 Metabolites

Publication date: Available online 24 October 2018Source: The Journal of Steroid Biochemistry and Molecular BiologyAuthor(s): Fumihiro Kawagoe, Toru Sugiyama, Kaori Yasuda, Motonari Uesugi, Toshiyuki Sakaki, Atsushi KittakaAbstractThree 23-hydroxylated vitamin D3 derivatives, which are metabolites of 25-hydroxyvitamin D3 produced by CYP24A1 and a related diastereomer, were efficiently synthesized. Each C23 hydroxy unit was constructed by the Claisen condensation reaction with ethyl acetate or the Grignard reaction with 2-methylallymagnesium chloride. Stereochemistry at the C23 position was determined by a modified Mosher’s method. The triene structures were constructed by the Wittig-Horner reaction utilizing the A-ring phosphine oxide moiety.Graphical Abstract
Source: The Journal of Steroid Biochemistry and Molecular Biology - Category: Biochemistry Source Type: research