Synthesis of casuarine-related derivatives via 1,3-dipolar cycloaddition between a cyclic nitrone and an unsaturated gamma-lactone.
The 1,3-dipolar cycloaddition of the cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to the single adduct 7 which can be transformed into the 3-epi-1-homo-casuarine via a reaction sequence involving reduction of the lactone moiety and N-O bond hydrogenolysis, followed by intramolecular alkylation of the nitrogen atom. The adduct 7 can also be used in the synthesis of 1-methyl- or 3-methyl analogues of 3-epi-casuarine.
Stecko
Sebastian
S
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Solecka
Jolanta
J
Chmielewski
Marek
M
D000470:Alkaloids / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis / Q000737:chemistry
D000470:Alkaloids; D007783:Lactones; D009589:Nitrogen Oxides; D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids; C409108:casuarine; C015388:nitrones