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A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (−)-16-Episilicine

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journal contribution
posted on 01.01.2010, 00:00 by Mercedes Amat, Núria Llor, Begoña Checa, Elies Molins, Joan Bosch
Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantioselective total synthesis of an alkaloid of the silicine group.