202402-58-2Relevant articles and documents
Ozonolysis of protected iridoid glucosides
Franzyk, Henrik,Rasmussen, Jon Holbech,Jensen, Soren Rosendal
, p. 365 - 370 (2007/10/03)
Scutellaria subvelutina was found to be an excellent source of the catalpol ester scutellarioside I (3) and this was chemically converted into 5,7-dideoxycynanchoside. The partially protected iridoid glucosides, 8,10:4′,6′-di-O-isopropylidene-5,7-dideoxycynanchoside (6) and 6,2′,3′,6′-tetra-O-benzoyl-antirrhinoside (10), as well as the fully protected 5,6-O-isopropylidene-2′,3′,4′,6′-tetra-O- acetylantirrhinoside (8a) were subjected to ozonolysis with reductive work-up using sodium tetrahydridoborate. Using a large excess of reductant, the reaction mixtures from 6 and 8a were reduced completely to give the respective poly substituted cyclopentanols, while reduction of the ozonolysis product from 10 could be stopped at the hemiacetal 11 by employing a smaller amount of reductant.