23-羟基化维生素 D 代谢物的简明合成。

Concise synthesis of 23-hydroxylated vitamin D metabolites.

机构信息

Faculty of Pharmaceutical Sciences, Teikyo University, 2-11-1 Kaga, Itabashi, Tokyo 173-8605, Japan; AMED-CREST, AMED, Japan.

Faculty of Pharmaceutical Sciences, Teikyo University, 2-11-1 Kaga, Itabashi, Tokyo 173-8605, Japan.

出版信息

J Steroid Biochem Mol Biol. 2019 Feb;186:161-168. doi: 10.1016/j.jsbmb.2018.10.010. Epub 2018 Oct 24.

DOI:10.1016/j.jsbmb.2018.10.010

PMID:30367940

Abstract

Three 23-hydroxylated vitamin D derivatives, which are metabolites of 25-hydroxyvitamin D 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.

摘要

三种 23-羟基维生素 D 衍生物，它们是由 CYP24A1 产生的 25-羟基维生素 D 的代谢产物，以及一种相关的非对映异构体，被有效地合成。每个 C23 羟基单元都是通过与乙酸乙酯的克莱森缩合反应或与 2-甲基烯丙基氯化镁的格氏反应构建的。C23 位的立体化学通过改进的 Mosher 法确定。三烯结构是通过利用 A 环膦氧化物部分的威蒂希-霍纳反应构建的。