TY - JOUR
T1 - Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine
AU - McCaig, Avril E.
AU - Meldrum, Kevin P.
AU - Wightman, Richard H.
PY - 1998/8/6
Y1 - 1998/8/6
N2 - Cycloadditions of 3,4-isopropylidenedioxy-?1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-?1-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.
AB - Cycloadditions of 3,4-isopropylidenedioxy-?1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-?1-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.
KW - Alkaloids
KW - Cycloadditions
KW - Indolizidines
KW - Pyrrolizidines
U2 - 10.1016/S0040-4020(98)00572-9
DO - 10.1016/S0040-4020(98)00572-9
M3 - Article
SN - 0040-4020
VL - 54
SP - 9429
EP - 9446
JO - Tetrahedron
JF - Tetrahedron
IS - 32
ER -