Total Synthesis of (+)-Hyacinthacine A2 Based on SmI2-Induced Nitrone Umpolung
datasetposted on 18.02.2005 by Stéphanie Desvergnes, Sandrine Py, Yannick Vallée
Datasets usually provide raw data for analysis. This raw data often comes in spreadsheet form, but can be any collection of data, on which analysis can be performed.
A 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.