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2005
Fused pyridine derivatives
R 0450
Stereoselective Synthesis of Polyhydroxylated Indolizidines Based on Pyridinium
Photochemistry and Ring Rearrangement Metathesis. — The cyclopentenes
08- 153 Salt
(I), (III) and (V), are generated by photochemical rearrangement of pyridinium salts,
smoothly undergo ring rearrangement metathesis to afford tetrahydropyridines. The
reaction of unsymmetrical substrates proceeds with high regioselectivity, which is governed by steric and thermodynamic effects. Tetrahydropyridines without an exocyclic
silyloxy group successfully undergo exocyclic dihydroxylation. The resulting diols can
smoothly be transformed into polyhydroxylated indolizidines. The derivative (VIII) is
a useful precursor of natural (-)-swainsonine (X). — (SONG, L.; DUESLER, E. N.;
MARIANO*, P. S.; J. Org. Chem. 69 (2004) 21, 7284-7293; Dep. Chem., Univ. N.
Mex., Albuquerque, NM 87131, USA; Eng.) — Jannicke
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