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Collective Syntheses of Guaiane Sesquiterpenes: Stereoselective Syntheses of (+)-Dysodensiol F, (+)-10β,14-Dihydroxy- allo -aromadendrane, and (-)-Dendroside C Aglycon.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2020 Nov 06; Vol. 85 (21), pp. 13779-13792. Date of Electronic Publication: 2020 Oct 13. - Publication Year :
- 2020
-
Abstract
- A collective synthetic route for tricyclic guaiane sesquiterpenes and total syntheses of (+)-dysodensiol F, (+)-10β,14-dihydroxy- allo -aromadendrane, and (-)-dendroside C aglycon starting from a versatile hydroazulene intermediate were accomplished. The key features of these syntheses involve late-stage carbene-mediated diastereoselective cyclopropanation, construction of an unusual cis- fused-hydroazulene skeleton via intramolecular Dieckmann condensation, and highly stereoselective tandem conjugate addition/intramolecular allylic alkylation to afford a 5/7/3 tricyclic skeleton of guaiane natural products. The synthesis of (-)-dendroside C aglycon and the first total synthesis of (+)-dysodensiol F and (+)-10β,14-dihydroxy- allo -aromadendrane are described in detail. Activation of the Nrf2/ARE signaling pathway by (-)-dendroside C aglycon is also disclosed via our synthesis.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 85
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 33049140
- Full Text :
- https://doi.org/10.1021/acs.joc.0c01907