[Substituted 16alpha,17alpha-cyclohexanopregnanes: the anionic oxy-Cope rearrangement of 3beta-tert-butyldimethylsilyloxy-19-hydroxy-19-vinyl-16alpha,17alpha-cyclohexapregn-5-en-20-one].
(19R)- and (19S)-tert-Butyldimethylsilyl (TBS) ethers of 19-hydroxy-19-vinyl-16alpha,17alpha-cyclohexanopregn-5-en-20-ones were synthesized. These compounds containing the 1,5-oxydienoic motif were subjected to the anionic oxy-Cope rearrangement to obtain 3beta-TBS ether of 6beta-(3-oxopropyl)-16alpha,17alpha-cyclohexano-19-nor-pregn-5(10)-en-20-one. The structures of the compounds synthesized were confirmed by the analysis of their H and 13C NMR spectra.
Levina
I S
IS
Kulikova
L E
LE
Shashkov
A S
AS
Galakhova
T N
TN
Kamernitskiĭ
A V
AV
D009682:Magnetic Resonance Spectroscopy; D011278:Pregnanes / Q000138:chemical synthesis* / Q000737:chemistry; D011283:Pregnenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
C523844:3beta-tert-butyldimethylsilyloxy-19-hydroxy-19-vinyl-16alpha,17alpha-cyclohexapregn-5-en-20-one; D011278:Pregnanes; D011283:Pregnenes