Configurative correlation and conformational analysis of strictosidine and vincoside derivatives
On the basis of the configuration of C-15 of the secologanin unit, using detailed NMR analysis, the configuration of C-3, the solution conformation around C-14, and the glucosidic bridge, as well as those of the dihydropyran and tetrahydropyridine rings, were determined in the vincosamide and strictosamide derivatives 4b and 5b. The stereochemical analysis was extended by chemical correlation to the 4-benzylated strictosidine and vincoside derivatives 3c and 3d. Experimental proof was presented for the interpretation of the "anomalous" chemical shift of acetylated strictosamide derivatives.
Patthy-Lukats
A
Institute of Organic Chemistry, Semmelweis University of Medicine, Hogyes u. 7, H-1092 Budapest, and Chinoin Pharmaceutical and Chemical Works, Ltd., To utca 1-5, H-1045 Budapest, Hungary.
Kocsis
A
Szabo
LF
Podanyi
B