title: Transannular Diels-Alder studies on the asymmetric total synthesis of chatancin: the pyranophane approach.
abstract: [reaction: see text] A pathway is proposed for the biosynthesis of (+)-chatancin and (+)-sarcophytin linking these tetracycles to cembranoids by a pyranophane transannular Diels-Alder reaction. Preliminary synthetic results in this direction to reach macrocyclic dienedione 28 from farnesol are reported. Major synthetic steps include a Prins reaction, two enantioselective hydrogenations, and a macrocyclization via a beta-ketosulfoxide Michael-addition on an enone.
authors.affiliation: Laboratoire de Synthèse Organique, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Quebec Canada.
authors.forename: A
authors.initials: A
authors.lastname: Toró
authors.forename: A
authors.initials: A
authors.lastname: L'Heureux
authors.forename: P
authors.initials: P
authors.lastname: Deslongchamps
mesh_terms: D000818:Animals; D003063:Cnidaria / Q000737:chemistry; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005204:Farnesol / Q000737:chemistry; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D010972:Platelet Activating Factor; C414662:chatancin; D005204:Farnesol