Formal Total Synthesis of (-)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes.
- 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 Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
- Roesslein J Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
- Kaufmann E Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
- Heikinheimo A Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
- Neuburger M Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
- Gademann K Department of Chemistry, University of Basel , St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
- 2016-10-15
Published in:
- The Journal of organic chemistry. - 2016
Carbon-13 Magnetic Resonance Spectroscopy
Cyclization
Proton Magnetic Resonance Spectroscopy
Sesquiterpenes
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
English
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.
- Language
-
- English
- Open access status
- green
- Identifiers
-
- DOI 10.1021/acs.joc.6b02039
- PMID 27740748
- Persistent URL
- https://sonar.ch/global/documents/91373
Statistics
Document views: 25
File downloads:
- Full-text: 0