Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity.
The potent antitumor agent OSW-1 was synthesized from the protected aglycone in different ways. It was proven that direct glycosylation of the aglycone in its hemiketal form could be achieved, affording the protected OSW-1 in a moderate yield. Alternatively, regioselective protection of the triol obtained by reduction of the aglycone, followed by glycosylation, deprotection and oxidation yielded the same OSW-1 derivative. The third approach to this compound consisted of glycosylation of the previously described lactol [Morzycki, J. W.; Gryszkiewicz, A. Polish J. Chem. 2001, 75, 983-989], reaction of the resulting aldehyde with a Grignard reagent, and oxidation. OSW-1 obtained on removal of the protective groups was identical with the natural product.
Morzycki
Jacek W
JW
Institute of Chemistry, University of Bialystok, al. Pilsudskiego 11/4, 15-443 Bialystok, Poland. morzycki@uwb.edu.pl
Wojtkielewicz
Agnieszka
A
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002783:Cholestenones / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D012503:Saponins / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D002783:Cholestenones; D007202:Indicators and Reagents; D012503:Saponins; C106408:OSW 1