The rearrangements of dihydrobetulin, dihydrobetulinic acid, and -lupane epoxides under acidic conditions (HCl, montmorillonite K10, and BF·EtO) were studied. The treatment of dihydrobetulin with HCl or K10 produced -lupane olefins. Their epoxidation afforded epoxides, which, in the presence of protic or Lewis acids, rearranged to dienes or lupanes bearing a bicyclo[3.
View Article and Find Full Text PDFSynthesis of lupane bidesmosides was optimized. The title compounds were obtained by glycosylation of 3-O- or 28-O-substituted betulin monodesmosides with Schmidt donors catalyzed by TMSOTf. Classical batch procedure and microreactor technique were used and compared in the above synthesis.
View Article and Find Full Text PDF