jo048237r_si_002.cif (22.38 kB)
Total Synthesis of (+)-Hyacinthacine A2 Based on SmI2-Induced Nitrone Umpolung
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posted on 2005-02-18, 00:00 authored by Stéphanie Desvergnes, Sandrine Py, Yannick ValléeA concise total synthesis of (+)-hyacinthacine A2, a polyhydroxylated pyrrolizidine alkaloid, is described using our
recently discovered inversion of the C−N bond polarity in
nitrones. In the key step, the diastereoselective reductive
coupling of a l-xylose-derived cyclic nitrone with ethyl
acrylate allowed the assembly of the bicyclic core of the
target molecule, by way of a tandem formation of the C−C
and C−N bonds. The method opens a novel, short, and
general route for the synthesis of other pyrrolizidine alkaloids.