Furans as Versatile Synthons: Total Syntheses of Caribenol A and Caribenol B

Hao, Hong-Dong and Trauner, Dirk (2017): Furans as Versatile Synthons: Total Syntheses of Caribenol A and Caribenol B. In: Journal of the American Chemical Society, Vol. 139, No. 11: pp. 4117-4122

Abstract

Two complex norditerpenoids, caribenols A and B, were accessed from a common building block. Our synthesis of caribenol A features the diastereoselective formation of the seven-membered ring through a Friedel-Crafts triflation and a late-stage oxidation of a furan ring. The first synthesis of caribenol B was achieved using an intramolecular organocatalytic alpha-arylation. An unusual intramolecular aldol addition was developed for the assembly of its cyclopentenone moiety, and the challenging trans-diol moiety was installed through a selective nucleophilic addition to a hydroxy 1,2-diketone. Our overall synthetic strategy, which also resulted in a second-generation synthesis of amphilectolide, confirms the usefulness of furans as powerful nucleophiles and versatile Synthons.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0002-7863
• Language: English