title: Mechanism for conversion of spirosolane derivative into pregnane.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan. none@ph.sojo-u.ac.jp
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Nohara
authors.forename: Kahori
authors.initials: K
authors.lastname: Okamoto
authors.forename: Sayaka
authors.initials: S
authors.lastname: Matsushita
authors.forename: Yukio
authors.initials: Y
authors.lastname: Fujiwara
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Ikeda
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Miyashita
authors.forename: Masateru
authors.initials: M
authors.lastname: Ono
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Yoshimitsu
authors.forename: Hisako
authors.initials: H
authors.lastname: Kansui
authors.forename: Takehisa
authors.initials: T
authors.lastname: Kunieda
mesh_terms: D006027:Glycosides / Q000737:chemistry*; D018551:Solanum lycopersicum / Q000737:chemistry*; D011278:Pregnanes / Q000138:chemical synthesis*; D012502:Sapogenins / Q000737:chemistry*
chemical_list: D006027:Glycosides; D011278:Pregnanes; D012502:Sapogenins; C505181:isoesculeogenin A