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Formal Total Synthesis of (-)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes.
Gomes, José; Daeppen, Christophe; Liffert, Raphael; Roesslein, Joel; Kaufmann, Elias; Heikinheimo, Annakaisa; Neuburger, Markus; Gademann, Karl.
Afiliación
  • Gomes J; Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
  • Daeppen C; Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
  • Liffert R; Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
  • Roesslein J; Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
  • Kaufmann E; Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
  • Heikinheimo A; Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
  • Neuburger M; Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
  • Gademann K; Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
J Org Chem ; 81(22): 11017-11034, 2016 11 18.
Article en En | MEDLINE | ID: mdl-27740748
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.
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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Sesquiterpenos Idioma: En Revista: J Org Chem Año: 2016 Tipo del documento: Article País de afiliación: Suiza Pais de publicación: Estados Unidos
Buscar en Google
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PubMed Links

Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Sesquiterpenos Idioma: En Revista: J Org Chem Año: 2016 Tipo del documento: Article País de afiliación: Suiza Pais de publicación: Estados Unidos