Facile conversion of 23-hydroxyspirosolane into pregnane

[Display omitted] Two novel reactions with regard to steroidal alkaloid sapogenols obtained from ripe tomato have been found. These reactions have been attained by simple facile method in only refluxing with pyridine and water. One is isomerization of a spirosolane derivative, isoesculeogenin A ( 2...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 20; pp. 3549 - 3551
Main Authors Matsushita, Sayaka, Yoshizaki, Miho, Fujiwara, Yukio, Ikeda, Tsuyoshi, Ono, Masateru, Okawara, Tadashi, Nohara, Toshihiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.05.2005
Elsevier
Subjects
Chemistry
Chemistry, Organic
Isomerization
Lycopersicon esculentum
Physical Sciences
Pregnane
Science & Technology
Solanocapsine
Spirosolane
Tomato steroidal alkaloids sapogenol
Pregnane
Tomato steroidal alkaloids sapogenol
Isomerization
Lycopersicon esculentum
Solanocapsine
Spirosolane
STEROIDAL ALKALOID GLYCOSIDES
FRUITS
spirosolane
isomerization
solanocapsine
tomato steroidal alkaloids sapogenol
pregnane
SOLANUM-ALKALOIDS
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] Two novel reactions with regard to steroidal alkaloid sapogenols obtained from ripe tomato have been found. These reactions have been attained by simple facile method in only refluxing with pyridine and water. One is isomerization of a spirosolane derivative, isoesculeogenin A ( 2 ), into a rare solanocapsine derivative, esculeogenin B ( 3 ), disclosing a chemical correlation between isoesculeogenin A and esculeogenin B. Another is conversion of a 23-hydroxyspirosolane derivative, esculeogenin A ( 1 ), into a pregnane derivative ( 4 ), presenting an epoch-making method for derivation of steroidal hormone material.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.03.116