title: Oxidative Prins-pinacol tandem process mediated by a hypervalent iodine reagent: scope, limitations, and applications.
abstract: An oxidative Prins-pinacol tandem process mediated by a hypervalent iodine reagent has been developed. This oxidative version of the famous tandem process fits within the concept of "aromatic ring umpolung" and allows the stereoselective transformation of simple phenols into highly elaborated spirocyclic dienone cores containing several quaternary carbon centers. The scope and the limitations of this process, including the study of its stereoselectivity, are described in this article. As a direct application of this stereoselective process, we describe the formal synthesis of (-)-platensimycin, an important antibiotic agent.
authors: Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, Montréal, H3C 3P8 Québec, Canada.
authors: Marc-André
authors: MA
authors: Beaulieu
authors: Kimiaka C
authors: KC
authors: Guérard
authors: Gaëtan
authors: G
authors: Maertens
authors: Cyrille
authors: C
authors: Sabot
authors: Sylvain
authors: S
authors: Canesi
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D062365:Aminobenzoates; D000813:Anilides; D007202:Indicators and Reagents; D010636:Phenols; D013141:Spiro Compounds; D007455:Iodine; D000218:Adamantane; C510909:platensimycin