Concise synthesis of 23-hydroxylated vitamin D3 metabolites
- Resource Type
- Authors
- Toru Sugiyama; Toshiyuki Sakaki; Atsushi Kittaka; Kaori Yasuda; Fumihiro Kawagoe; Motonari Uesugi
- Source
- The Journal of Steroid Biochemistry and Molecular Biology. 186:161-168
- Subject
- 0301 basic medicine
Phosphine oxide
Vitamin
Claisen condensation
Endocrinology, Diabetes and Metabolism
Clinical Biochemistry
Grignard reaction
Ethyl acetate
Diastereomer
Cell Biology
Biochemistry
Chloride
03 medical and health sciences
chemistry.chemical_compound
030104 developmental biology
0302 clinical medicine
Endocrinology
chemistry
030220 oncology & carcinogenesis
medicine
Molecular Medicine
Moiety
Organic chemistry
Molecular Biology
medicine.drug
- Language
- ISSN
- 0960-0760
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.