Wisconsin Alumni Research Foundation

David E Hamer

Hector Floyd Deluca

Heinrich K Schnoes

Herbert E Paaren

A process for preparing biologically active 1.alpha.-hydroxyvitamin D compounds from vitamin D compounds by hydroxylation at carbon 1 and subsequent photochemical isomerization, and novel intermediates and products resulting from this process are provided.

1-Hydroxylation process

A method for preparing 1.alpha.-hydroxylated vitamin D compounds from 5,6-trans-vitamin D compounds which comprises allylically oxidizing a 5,6-trans-vitamin D compound, subjecting the oxidation product to actinic radiation in the presence of a photosensitizing agent and recovering the 1.alpha.-hydroxylated compound. 1.alpha.-hydroxylation is recognized as being essential to impart biological activity to vitamin D compounds and their derivatives. The present invention provides an efficient method for maximizing the yield of 1.alpha.-hydroxylated vitamin D compounds.

Process for preparing 1-hydroxylated vitamin D compounds from

An improved method for the preparation of 1.alpha.-hydroxylated vitamin D compounds involving directly introducing an oxygen function at carbon 1 of the vitamin D molecule or precursors or derivatives thereof, wherein the 1.alpha.-hydroxycyclovitamin D intermediate is solvolyzed directly, without first converting the 1-hydroxy group to a 1-O-acyl function as a protective measure.

Process for preparing 1.alpha.-hydroxylated compounds

A method for preparing 1.alpha.-hydroxyvitamin D compounds from 1.alpha.-hydroxy-3,5-cyclovitamin D compounds which comprises solvolyzing the 3,5-cyclovitamin D compound, exposing the solvolysis reaction products to actinic radiation in the presence of a photosensitizing agent and recovering the 1.alpha.-hydroxylated vitamin D compounds. 1.alpha.-hydroxylation is recognized as being essential to impart biological activity to vitamin D compounds and their derivatives. The present invention provides an efficient method for maximizing the yield of 1.alpha.-hydroxylated vitamin D compounds.

Process for preparing 1.alpha.-hydroxyvitamin D compounds from

A method for directly introducing an oxygen function at carbon 1 of the vitamin D molecule or precursors of derivatives thereof which comprises subjecting such molecules to allylic oxidation utilizing selenium dioxide as the oxidizing agent.

A method for directly introducing an oxygen function at carbon 1 of the vitamin D molecule or precursors or derivatives thereof which comprises subjecting such molecules to allylic oxidation utilizing selenium dioxide as the oxidizing agent.

Growing community of inventors

Madison, WI, United States of America

David E Hamer