A simple and efficient enantioselective route to 2,6-disubstituted piperidines: synthesis of (2R,6S)-isosolenopsin A and (2S,6R)-isosolenopsin |
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| Authors: | R. Sateesh Chandra Kumar Eppakayala Sreedhar G. Venkateswar Reddy K. Suresh Babu J. Madhusudana Rao |
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| Affiliation: | Natural Products Laboratory, Organic Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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| Abstract: | The enantioselective synthesis of 2,6-cis-disubstituted piperidine alkaloids, (2R,6S)-isosolenopsin A 2 and (2S,6R)-isosolenopsin 5 from fire ant venom is described. Starting from the dodecanal and decanal, the synthesis presents two key steps. The first step involves Keck allylation to afford the chiral homoallylalcohol with the required stereochemistry and the second key step consists of Grubbs olefin cross metathesis. The synthesis was achieved in five steps with 44% overall yield. |
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