Concise synthesis of 23-hydroxylated vitamin D3 metabolites. Issue 186 (February 2019)

• Record Type: Journal Article
• Authors: Kawagoe, Fumihiro; Sugiyama, Toru; Yasuda, Kaori; Uesugi, Motonari; Sakaki, Toshiyuki; Kittaka, Atsushi
• Is Part Of: Journal of steroid biochemistry and molecular biology. Issue 186(2019)
• Page Start: 161
• Page End: 168
• Publication Date: 2019-02
• Subjects: Synthesis -- 23-Hydroxyvitamin D3 -- Vitamin D3 metabolite -- Modified Mosher's method; Steroid hormones -- Periodicals; Biochemistry -- Periodicals; Hormones -- Periodicals; Molecular Biology -- Periodicals; Hormones stéroïdes -- Périodiques; Steroid hormones; Periodicals; 572.579
• DOI: 10.1016/j.jsbmb.2018.10.010
• Languages: English
• ISSNs: 0960-0760

Abstract

Graphical abstract: Highlights: CYP24A1 metabolites of 25-hydroxyvitamin D3 were efficiently synthesized. The Claisen condensation was used for the 23, 25-dihydroxyvitamin D3 metabolite. 23, 25, 26-Trihydroxyvitamin D3 was synthesized using Grignard reaction. Abstract: Three 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.