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A concise synthetic pathway towards 5-substituted indolizidines |
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| Authors: | Tamás R Varga Péter Nemes Zoltán Mucsi Pál Scheiber |
| Institution: | Department of Chemistry, Faculty of Veterinary Science, Szent István University, H-1400 Budapest, PO Box 2, Hungary |
| Abstract: | The total synthesis of 5-(2′-hydroxyethyl)indolizidine via 5-thioindolizidinone is described. The key step is the transformation of 5-thioindolizidinone via Eschenmoser’s sulfide contraction. The racemic mixture of 5R,9R- and 5S,9S-5-(2′-hydroxyethyl)indolizidine was obtained in seven steps in 17% overall yield from 2-allyl cyclopentanone. |
| Keywords: | Eschenmoser&rsquo s sulfide contraction 5-Thioindolizidinone 5-Substituted indolizidines 2-Allyl cyclopentanone |
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