title: Asymmetric synthesis of the main core of kaurane family members triggered by an oxidative polycyclization-pinacol tandem process.
abstract: Polycyclization processes represent expeditious routes used in both nature and the laboratory to produce complex polycyclic molecules. A new stereoselective oxidative variant of such a polycyclization has been developed in which the cascade is triggered by a phenol dearomatization and is concluded by a pinacol transposition. This unprecedented avenue combines the synthetic power of a polycyclization and a transposition in tandem and enables the rapid formation of the tetracyclic main core of kaurane diterpenes containing several asymmetric and quaternary carbon centers in a single step from a simple phenol derivative.
authors.affiliation: Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal , C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada.
authors.forename: Samuel
authors.initials: S
authors.lastname: Desjardins
authors.forename: Gaëtan
authors.initials: G
authors.lastname: Maertens
authors.forename: Sylvain
authors.initials: S
authors.lastname: Canesi
mesh_terms: D002384:Catalysis; D003500:Cyclization; D045786:Diterpenes, Kaurane / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D045786:Diterpenes, Kaurane; D010636:Phenols