Mechanism for conversion of spirosolane derivative into pregnane.
Previously, we reported an interesting reaction by which esculeogenin A [(5alpha,22S,23S,25S)-3beta,23,27-trihydroxyspirosolane], a sapogenol of tomato-saponin, esculeoside A, was easily converted into a pregnane derivative, 5alpha-pregn-16-en-3beta-ol-20-one, merely by refluxing with pyridine and water. Its chemical mechanism including air oxidation is here described.
Nohara
Toshihiro
T
Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan. none@ph.sojo-u.ac.jp
Okamoto
Kahori
K
Matsushita
Sayaka
S
Fujiwara
Yukio
Y
Ikeda
Tsuyoshi
T
Miyashita
Hiroyuki
H
Ono
Masateru
M
Yoshimitsu
Hitoshi
H
Kansui
Hisako
H
Kunieda
Takehisa
T
D006027:Glycosides / Q000737:chemistry*; D018551:Solanum lycopersicum / Q000737:chemistry*; D011278:Pregnanes / Q000138:chemical synthesis*; D012502:Sapogenins / Q000737:chemistry*
D006027:Glycosides; D011278:Pregnanes; D012502:Sapogenins; C505181:isoesculeogenin A