Synthesis of "glycospirostanes"--steroid sapogenins with a sugar-like ring F.
The synthesis of two "glycospirostanes" from 23-oxotigogenin acetate is described. (23S,24S,25R)-5alpha-Spirostane-3beta,23,24,25-tetraol was obtained by dehydrogenation followed by stereoselective reduction of the 23-oxo group and OsO(4) dihydroxylation of the C24-C25 double bond. Allylic hydroxylation with SeO(2) of 3beta-acetoxy-5alpha-spirost-23-ene obtained from 23-oxotigogenin acetate followed by OsO(4) dihydroxylation of the C23-C24 double bond afforded (23R,24S,25R)-5alpha-spirostane-3beta,23,24,25-tetraol.
López
Yliana
Y
Institute of Chemistry, University of Białystok, Piłsudskiego 11/4, 15-443 Białystok, Poland.
Jastrzebska
Izabella
I
Santillan
Rosa
R
Morzycki
Jacek W
JW
D018360:Crystallography, X-Ray; D008956:Models, Chemical; D015394:Molecular Structure; D012502:Sapogenins / Q000138:chemical synthesis* / Q000737:chemistry*; D013150:Spirostans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D012502:Sapogenins; D013150:Spirostans