1091-89-0Relevant academic research and scientific papers
C(10)-C(19) bond cleavage reaction of 19-oxygenated androst-4-ene-3,6-dione steroids under various conditions
Nagaoka, Masao,Numazawa, Mitsuteru
, p. 983 - 985 (2004)
C(10)-C(19) bond cleavage reaction of 19-hydroxy- and 19-oxoandrost-4-ene- 3,6,17-triones (5, 6) was explored under various conditions. Treatment of steroids 5 and 6 with KOH in MeOH gave the A-ring aromatized product 6-oxoestrone (11) in a fair yield, respectively, in contrast, the treatment with a weak base yielded 4-methyl steroid 17 (20%) in the case of 19-alcohol 5 or 19-nor- Δ5(10)-steroid 9 (12-67%) along with compound 11 (6-27%) in the case of 19-aldehyde 6. Reaction of compound 6 with HCl in MeOH produced 3-methyl ethers of 6-oxoestrone and Δ6-estrone, compounds 12 and 14 (ca. 20% each). Thus, 6-oxosteroids 5 and 6 showed unique C(10)-C(19) bond cleavage reactions with a base or acid.
1,4-Addition reaction with thiols and conformational analysis with PM3 molecular orbital calculations of 19-oxygenated androst-4-ene-3,6,17-triones
Numazawa,Oshibe,Matsuzaki
, p. 423 - 428 (2007/10/02)
Reactions of androst-4-ene-3,6,17-trione (1) and its 19-hydroxy or 19-oxo derivative (2 or 3), suicide substrates of aromatase, with thiols were initially studied. Treatment of 4-ene-3,6-diones 1-3 with benzyl-mercaptan in MeOH at room temperature gave th
