@article{3054510, title = "Selective amination of secoiridoid glycosides to give monomeric pyridine, dimeric pyridine, and naphthyridine alkaloids", author = "Ranarivelo, Y and Magiatis, P and Skaltsounis, AL and Tillequin, F", journal = "NATURAL PRODUCT LETTERS", year = "2001", volume = "15", number = "2", pages = "131-137", publisher = "TAYLOR & FRANCIS LTD LONDON", issn = "1057-5634", doi = "10.1080/10575630108041270", keywords = "secoiridoids; monoterpene alkaloids; pyridines; naphthyridines", abstract = "Treatment of the secoiridoids oleuropein (4), ligstroside (5) and methyloleoside (6) by beta -D-glucosidase in the presence of ammonium chloride led exclusively to monomeric pyridine alkaloids 7, 1, and 8. Dimeric 3,4,5-trisubstituted pyridines were obtained from methyloleoside (6) when ammonium chloride was generated in the reaction mixture by successive additions of ammonia and hydrochloric acid. The use of ammonium acetate permitted conversion of secoiridoids 4 and 5 into the naphthyridine alkaloid jasminine (3)." }