A copper-catalyzed double coupling enables a 3-step synthesis of the quassinoid core architecture. Issue 3 (6th November 2018)

• Record Type: Journal Article
• Authors: Condakes, Matthew L.; Rosen, Rachel Z.; Harwood, Stephen J.; Maimone, Thomas J.
• Is Part Of: Chemical science. Volume 10:Issue 3(2019)
• Page Start: 768
• Page End: 772
• Publication Date: 2018-11-06
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc03835j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A cross coupling/SN 2′ tandem reaction is described to construct the polycyclic core architecture of the quassinoids, a fascinating class of degraded triterpenes with potent anticancer activity. Abstract : The quassinoids are a fascinating class of degraded triterpene natural products which possess, among other attributes, potent anti-cancer activity. Their complex polycyclic ring systems also serve as inspiration for the development of new chemical methods and strategies – especially those pertaining to C–C bond formation. Herein we disclose a novel tandem cross coupling/SN 2′ reaction of vicinal epoxy vinyl triflates with simple Grignard reagents catalyzed by Cu(i ). Using this transformation, the polycyclic core architecture of the quassinoids can be generated in only three linear steps from carvone epoxide, forming five carbon–carbon bonds in the process.