Synthesis of pyrrolizidine alkaloids via 1,3-dipolar cycloaddition involving cyclic nitrones and unsaturated lactones.
The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 2,6-dihydroxyhastanecine via reaction sequence involving reduction of the lactone moiety, glycolic cleavage of the terminal diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom.
Stecko
Sebastian
S
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Jurczak
Margarita
M
Urbańczyk-Lipkowska
Zofia
Z
Solecka
Jolanta
J
Chmielewski
Marek
M
D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D002621:Chemistry / Q000379:methods; D018360:Crystallography, X-Ray / Q000379:methods; D006859:Hydrogen / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature
D002241:Carbohydrates; D007783:Lactones; D009589:Nitrogen Oxides; D011763:Pyrrolizidine Alkaloids; C015388:nitrones; D006859:Hydrogen