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Synthesis of new 16-spirosteroids
L F Tietze1, J Wölfling, G Schneider
1Institute of Organic Chemistry, Georg-August University, Göttingen, Germany.
Steroids
|May 1, 1994
Abstract:
Reaction of estrone methyl ether 1 with sodium hydride and 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane, respectively, gives the 16-spirosteroid derivatives 2-4, which were reduced to the 17 beta-alcohols 7-9. Acetylation afforded the acetates 10-12. In the reaction of 1 and 1,3-dibromopropane a bis-allyl compound 5 and an annulated dihydropyran 6 were also formed. Cleavage of the ether moiety in 2 and 3 was accomplished with diisobutylaluminum hydride to give 3,17 beta-diols 13 and 14, respectively.