Synthesis of "glycospirostanes" via ring-closing metathesis.
Syntheses of "glycospirostanes" from 3beta-hydroxy-23,24-dinor-5alpha-cholano-22,16-lactone and 3alpha-hydroxy-23,24-dinor-5beta-cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivative. Further elaboration of the six-membered ring F consisted of allylic hydroxylation with SeO(2) followed by OsO(4) dihydroxylation of the C24-C25 double bond. The obtained final products proved to be simultaneously O- and C-l-arabinopyranosides.
Czajkowska
Dorota
D
Institute of Chemistry, University of Białystok, Piłsudskiego 11/4, Białystok, Poland.
Morzycki
Jacek W
JW
Santillan
Rosa
R
Siergiejczyk
Leszek
L
D009654:Norsteroids / Q000138:chemical synthesis / Q000737:chemistry*; D013150:Spirostans / Q000138:chemical synthesis* / Q000737:chemistry
C546983:3-hydroxy-23,24-dinorcholano-22,16-lactone; D009654:Norsteroids; D013150:Spirostans; C046297:sarsasapogenin