Synthesis of novel alkaloid derivatives from vinyl ether of lupinine and PH-addends
Nina K. GusarovaIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, RussiaSvetlana F. MalyshevaIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, RussiaLudmila A. OparinaIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, RussiaNataliya A. BelogorlovaIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, RussiaА. П. ТанцыревIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, RussiaL. N. ParshinaIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, RussiaБ. Г. СуховIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, RussiaRustam T. TlegenovKarakalpakstan State University, 1 akad. Abdirova Street, Nukus 742012, Karakalpak Republic, UzbekistanБ. А. ТрофимовIrkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
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A new family of functional quinolizidine alkaloids containing alkoxy groups and phosphine or phosphine chalcogenide fragments has been prepared from the vinyl ether of enantiomerically pure lupinine, secondary phosphines and phosphine sulfide. The reaction proceeds readily under radical initiation to give anti-Markovnikov adducts, dialkyl[2-(octahydro-2H-quinolizin-1ylmethyloxy)ethyl]phosphines and -phosphine sulfide, in high yields (89-96%). The phosphine moieties of the alkaloids synthesized have been oxidized with air, elemental sulfur or selenium to afford the corresponding phosphine chalcogenides.
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