Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 4, Pages 1459-1462Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo048237r
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A concise total synthesis of (+)-hyacinthacine A(2), 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.
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