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

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-de...

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Veröffentlicht in:Journal of the American Chemical Society 2017-12, Vol.139 (49), p.17783-17786
Hauptverfasser: Condakes, Matthew L, Hung, Kevin, Harwood, Stephen J, Maimone, Thomas J
Format: Artikel
Sprache:eng
Schlagworte:
Biological Products - chemical synthesis
Biological Products - chemistry
Communication
Illicium - chemistry
Molecular Structure
Oxidation-Reduction
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Terpenes - chemistry
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b11493