Asymmetric synthesis of fortucine and reassignment of its absolute configuration.
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.
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.
Marc-André
MA
Beaulieu
Xavier
X
Ottenwaelder
Sylvain
S
Canesi
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; C526926:fortucine
aromatic ring umpolung; hypervalent iodine; natural products; oxidation; total synthesis