Total Synthesis of (+)-Hyacinthacine A2 Based on SmI2-Induced Nitrone Umpolung.
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| Title: | Total Synthesis of (+)-Hyacinthacine A |
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| Authors: | Desvergnes, Stephanie1, Py, Sandrine1 sandrine.py@ujf-grenoble.fr, Vallée, Yannick1 |
| Source: | Journal of Organic Chemistry. 2/18/2005, Vol. 70 Issue 4, p1459-1462. 4p. 3 Diagrams. |
| Subjects: | Pyrrolizidines, Chemical bonds, Alkaloids, Cyclic compounds, Chemicals, Chemical reactions |
| Abstract: | 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. [ABSTRACT FROM AUTHOR] |
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| Database: | Engineering Source |
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