Direct C-1 hydroxylation of vitamin D compounds: convenient preparation of 1alpha-hydroxyvitamin D3, 1alpha, 25-dihydroxyvitamin D3, and 1alpha-hydroxyvitamin D2.
- 1 May 1978
- journal article
- research article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 75 (5), 2080-2081
- https://doi.org/10.1073/pnas.75.5.2080
Abstract
An efficient procedure for the direct C-1 hydroxylation of vitamin D compounds was developed. The method involves conversion of vitamin D3 tosylates to 3,5-cyclovitamin D derivatives, allylic oxidation with selenium dioxide and acid-catalyzed solvolysis to the 1.alpha.-hydroxyvitamin D analogs. When applied to vitamin D3, 25-hydroxyvitamin D3 and vitamin D2, this sequence gives the corresponding 1.alpha.-hydroxylated derivatives in 10-15% yield.This publication has 5 references indexed in Scilit:
- Conformational equilibriums in vitamin D. Synthesis of 1.beta.-hydroxyvitamin D3The Journal of Organic Chemistry, 1977
- The selenium dioxide oxidation of cholecalciferolSteroids, 1977
- Metabolism and Mechanism of Action of Vitamin DAnnual Review of Biochemistry, 1976
- Vitamin D-3,5-cyclovitamin D rearrangementJournal of the American Chemical Society, 1975
- 1α-Hydroxyvitamin D 2 : A Potent Synthetic Analog of Vitamin D 2Science, 1974