title: Total synthesis of cyclic diterpene tonantzitlolone based on a highly stereoselective substrate-controlled aldol reaction and ring-closing metathesis.
abstract: The total synthesis of the cyclic diterpene ent-tonantzitlolone (ent-1) is presented. Key steps for assembling the macrocyclic core structure of 1 are a highly selective aldol reaction and an E selective ring-closing metathesis reaction. A detailed investigation of these two steps and the final transformations towards the completion of the synthesis is disclosed.
authors.affiliation: Universität Basel, Departement Chemie, Spitalstrasse 51, 4065 Basel, Switzerland.
authors.forename: Christian
authors.initials: C
authors.lastname: Jasper
authors.forename: Alexander
authors.initials: A
authors.lastname: Adibekian
authors.forename: Torsten
authors.initials: T
authors.lastname: Busch
authors.forename: Monika
authors.initials: M
authors.lastname: Quitschalle
authors.forename: Rüdiger
authors.initials: R
authors.lastname: Wittenberg
authors.forename: Andreas
authors.initials: A
authors.lastname: Kirschning
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D008956:Models, Chemical; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D047028:Macrocyclic Compounds; C510266:tonantzitlolone