Total synthesis of (-)-himgaline |
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| Authors: | Shah Unmesh Chackalamannil Samuel Ganguly Ashit K Chelliah Mariappan Kolotuchin Sergei Buevich Alexei McPhail Andrew |
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| Affiliation: | Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA. |
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| Abstract: | The first total synthesis of (-)-himgaline and a highly enantioselective synthesis of its congener (-)-GB 13 are described. Decarboxylative aza-Michael reaction of the hexacyclic lactone precursor under acidic conditions, followed by basic workup, yielded (-)-GB 13 in 80% yield. Cyclization of (-)-GB 13 to oxohimgaline under acidic conditions, followed by internally coordinated sodium triacetoxyborohydride reduction, gave (-)-himgaline as the exclusive product. |
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