Total synthesis of (+)-hyacinthacine A2 based on SmI2-induced nitrone umpolung |
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Authors: | Desvergnes Stéphanie Py Sandrine Vallée Yannick |
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Institution: | LEDSS, UMR 5616 CNRS Institut de Chimie Moléculaire de Grenoble - FR 2607 Université Joseph Fourier, B.P. 53, 38041 Grenoble, France. |
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Abstract: | reaction: see text] 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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