Enantioselective synthesis of 2-[(3-ethyl-4-piperidyl)methyl]indoles from a phenylglycinol-derived lactam: formal synthesis of Strychnos alkaloids |
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| Authors: | Mercedes Amat |
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| Institution: | Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona, Spain |
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| Abstract: | A diastereodivergent synthesis of enantiopure cis- and trans-2-(3-ethyl-4-piperidyl)methyl]indole (cis-1b and trans-1b) from a common phenylglycinol-derived oxazolopiperidone lactam 3 is reported. The key step is a stereocontrolled conjugate addition, either under kinetic or thermodynamic control, of the dilithium salt of 2-(2-indolyl)-1,3-dithiane to unsaturated lactam 3. |
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| Keywords: | Phenylglycinol Strychnos alkaloids Piperidines Indoles Oxazolopiperidone lactams |
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