- Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine
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Cycloadditions of 3,4-isopropylidenedioxy-Δ1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-Δ1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.
- McCaig, Avril E.,Meldrum, Kevin P.,Wightman, Richard H.
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p. 9429 - 9446
(2007/10/03)
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