Isolation of steroids containing a 5,7-diene functionality...

Details Isolation of steroids containing a 5,7-diene functionality... Isolation of steroids containing a 5,7-diene functionality...

C - Chemistry, Metallurgy

07

J

C07J 9/00 (2006.01) C07C 401/00 (2006.01) C07J 7/00 (2006.01)

Patent

CA 2118122

A method is provided for isolating 5,7-diene-containing steroids, particularly 3 .beta.-ols and esters of 3 .beta.-ols, from a sterol mixture. The method involves (1) treating the mixture with a dienophile or with an oxidizable dienophile precursor in combina- tion with an oxidizing agent so as to provide a Diels-Alder adduct of the 5,7- diene to be isolated, followed by (2) removal of the adduct from the mixture and (3) regeneration of the 5,7-diene with a suitable reducing agent. The invention also encompasses subsequent purification steps and intermediate modification of the Diels-Alder intermediate, e.g., wherein chemical conversion of the Diels-Alder adduct is effected prior to regeneration of the 5,7-diene. Novel compounds which are Diels-Alder adducts of 5,7-diene-containing steroids are provided as well.

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