Synthesis of 1.alpha.-hydroxy-7-dehydrosteroids
AssigneeDiamond Shamrock Corporation
InventorsWilliam H. Klausmeier, Richard L. Johnson, Arnold L. Hirsch
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Abstract
Enol acetylation is carried out on a variety of 1,4,6-trien-3-ones to form 1,3,5,7 tetraene structures from which 1.alpha.-hydroxy-7-dehydro steroids are obtained. The compounds are intermediates used in the preparation of vitamin D.sub.3 metabolites such as 1.alpha.,25-dihydroxyvitamin D.sub.3 and 1.alpha.-hydroxyvitamin D.sub.3.
Claims14
A steroid compound having the structure:
- ##STR30## where R is selected from the group consisting of C.sub.8 H.sub.16 OH;
- C.sub.8 H.sub.16 O.sub.2 CCH.sub.3 ;
- ##STR31## and C.sub.5 H.sub.8 O.sub.2 CH.sub.3 and where R'CO-- is the residue of an acylating agent.
Cholesta-1,3,5,7-tetraene-3,25-diol 3-acetate 25-benzoate.
Methyl 3-acetoxychola-1,3,5,7-tetraen-24-oate.
An enol acetylation process comprising reacting a steroid containing:
- ##STR32## with an acylating agent forming the corresponding .DELTA.1,3,5,7-Tetraene-enol acetate.
An enol acetylation process comprising reaction with an acylating agent to form the corresponding .DELTA.1,3,5,7-Tetraene-enol acetate a steroid of the following structure:
- ##STR33## where:
- ##STR34## and where Z is the above, a is 3, ##STR35## and where Z is the above, a is 0, 1, 2 or 3, ##STR36## and where Z is the above, a is 2, and ##STR37## and where Z is the above, a is 0, 1, 2 or 3, and R' is hydrogen, alkyl or aryl.
Dependencies are inferred from the claim text.