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Asymmetric Synthesis of Fortucine and Reassignment of Its Absolute Configuration |
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| Authors: | Marc‐André Beaulieu Prof. Xavier Ottenwaelder Prof. Sylvain Canesi |
| Affiliation: | 1. Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre‐Ville, Montréal, QC, H3C 3P8 (Canada), Fax: (+1)?514‐987‐4054;2. Department of Chemistry and Biochemistry, Concordia University, 7141 Sherbrooke W, Montreal, QC, H4B 1R6 (Canada) |
| Abstract: | A convergent and enantioselective synthesis of fortucine was achieved from the starting materials tyrosine methyl ester and 3‐hydroxy‐4‐methoxybenzaldehyde. The synthesis is based on two key steps mediated by a hypervalent iodine reagent. This work has enabled us to reassign the absolute configuration of the natural product reported in the literature. |
| Keywords: | aromatic ring umpolung hypervalent iodine natural products oxidation total synthesis |