Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one |
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Authors: | Paul Armstrong Paul J. Stevenson Andrew D. Walker |
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Affiliation: | a School of Chemistry, Queen’s University, Belfast BT9 5AG, Ireland b CSS Ltd, Almac House, 20 Seagoe Industrial Estate, Craigavon BT63 5PW, Ireland |
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Abstract: | Catalytic hydrogenation of dihydroindolizidinone occurred preferentially from the endo-face giving rapid entry to (8R,8aS)-8-methylhexahydroindolizin-5-one, a key intermediate in the synthesis of 5,8-disubstituted indolizidines and deoxypumiliotoxin 251H. The selectivity could be improved further by diimide reduction though this also resulted in some oxidation of the alkene to the diene. The basis of the unusual stereoselectivity in the diimide reduction is believed to be stereoelectronic in origin. |
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Keywords: | Indolizidines Stereoelectronic Cieplak effect |
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