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Synfacts 2023; 19(07): 0637
DOI: 10.1055/s-0042-1752559
DOI: 10.1055/s-0042-1752559
Synthesis of Natural Products
Syntheses of (–)-Scabrolide A and (–)-Yonarolide
Autoren
Serrano R,
Boyko YD,
Hernandez LW,
Lotuzas A,
Sarlah D.
*
University of Illinois, Urbana, USA
Total Syntheses of Scabrolide A and Yonarolide.
J. Am. Chem. Soc. 2023;
145: 8805-8809
DOI: 10.1021/jacs.3c02317
Total Syntheses of Scabrolide A and Yonarolide.
J. Am. Chem. Soc. 2023;
145: 8805-8809
DOI: 10.1021/jacs.3c02317
Key words
(–)-scabrolide A - (–)-yonarolide - norcembranoid terpenoids - Ni-catalyzed annulation - Riley oxidation - Liebeskind–Srogl coupling - intramolecular Michael addition/elimination
Significance
Sarlah and co-workers report the total syntheses of (–)-scabrolide A and (–)-yonarolide, two norcembranoid terpenoids. The natural products feature a 5/6/7-fused carbocyclic ring system and an additional γ‑lactone.
Comment
Bicyclic lactone F is accessed by Ni‑catalyzed annulation using cyclopropane C and subsequent fragmentation. The two building blocks F and H were fused in a Liebeskind–Srogl coupling. An intramolecular Michael addition elimination cascade using a zinc-amido base furnishes enone L.
Publikationsverlauf
Artikel online veröffentlicht:
16. Juni 2023
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