Total Syntheses of ( −)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes

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(sp3)-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.

Source: Organometallic Current - November 28, 2017 Category: Chemistry Tags: Total synthesis Source Type: blogs