Synthesis of trihydroxylated pyrrolizidine and indolizidine alkaloids based on SmI2-induced reductive coupling of chiral nitrones with methyl acrylate |
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| Authors: | Juraj Rehá kLubor Fi&scaron era,Jozef Ko?í &scaron ekLenka Bellovi?ová |
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| Affiliation: | a Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, SK-812 37 Bratislava, Slovak Republic
b Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, SK-812 37 Bratislava, Slovak Republic |
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| Abstract: | Synthesis of trihydroxylated pyrrolizidines, the enantiomer of 2-epihyacinthacine A2 and indolizidine analogues of the natural alkaloids is reported. The key step of these syntheses is the stereoselective samarium diodide-induced coupling of the chiral nitrone prepared from d-ribose with methyl acrylate. The nitrone derived from d-ribose possessing C2/C3 syn configuration reacted with methyl acrylate in the presence of samarium diiodide in excellent yield and diastereoselectivity, with only the anti-diastereomer being detected. |
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| Keywords: | Pyrrolizidine Indolizidine Alkaloids Nitrones Samarium diiodide |
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