title: Formal Total Synthesis of (-)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes.
abstract: Synthetic studies toward highly oxygenated seco-prezizaane sesquiterpenes are reported, which culminated in a formal total synthesis of the neurotrophic agent (-)-jiadifenolide. For the construction of the tricyclic core structure, an unusual intramolecular and diastereoselective Nozaki-Hiyama-Kishi reaction involving a ketone as electrophilic coupling partner was developed. In addition, synthetic approaches toward the related natural product (2R)-hydroxy-norneomajucin, featuring a Mn-mediated radical cyclization for the tricycle assembly and a regioselective OH-directed C-H activation are presented.
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
authors.forename: José
authors.initials: J
authors.lastname: Gomes
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.|Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Christophe
authors.initials: C
authors.lastname: Daeppen
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.|Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Raphael
authors.initials: R
authors.lastname: Liffert
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.|Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Joel
authors.initials: J
authors.lastname: Roesslein
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.|Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Elias
authors.initials: E
authors.lastname: Kaufmann
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
authors.forename: Annakaisa
authors.initials: A
authors.lastname: Heikinheimo
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
authors.forename: Markus
authors.initials: M
authors.lastname: Neuburger
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.|Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Karl
authors.initials: K
authors.lastname: Gademann
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D003500:Cyclization; D066244:Proton Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; C546282:jiadifenolide