| Autor: |
Condakes ML; Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States., Hung K; Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States., Harwood SJ; Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States., Maimone TJ; Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States. |
| Abstrakt: |
We report the first chemical syntheses of both (-)-majucin and (-)-jiadifenoxolane A via 10 net oxidations from the ubiquitous terpene (+)-cedrol. Additionally, this approach allows for access to other majucin-type sesquiterpenes, like (-)-jiadifenolide, (-)-jiadifenin, and (-)-(1R,10S)-2-oxo-3,4-dehydroxyneomajucin (ODNM) along the synthetic pathway. Site-selective aliphatic C(sp 3 )-H bond oxidation reactions serve as the cornerstone of this work which offers access to highly oxidized natural products from an abundant and renewable terpene feedstock. |
