Synthesis of new 16-spirosteroids.
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.
Tietze
L F
LF
Institute of Organic Chemistry, Georg-August University, Göttingen, Germany.
Wölfling
J
J
Schneider
G
G
Noltemeyer
M
M
D000107:Acetylation; D003460:Crystallization; D004970:Estrone / Q000031:analogs & derivatives* / Q000737:chemistry*; D005663:Furans; D006842:Hydrocarbons, Brominated; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010420:Pentanes; D011407:Propane / Q000031:analogs & derivatives; D013055:Spectrophotometry, Infrared; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D005663:Furans; D006842:Hydrocarbons, Brominated; D010420:Pentanes; D013141:Spiro Compounds; C089051:1,5-dibromopentane; D004970:Estrone; C018674:tetrahydrofuran; C050754:1,4-dibromobutane; D011407:Propane; C032699:1,3-dibromopropane