title: Furans as Versatile Synthons: Total Syntheses of Caribenol A and Caribenol B.
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 α-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.
authors.affiliation: Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Hong-Dong
authors.initials: HD
authors.lastname: Hao
authors.affiliation: Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Dirk
authors.identifier: 0000-0002-6782-6056
authors.initials: D
authors.lastname: Trauner
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D008968:Molecular Conformation
chemical_list: D004224:Diterpenes; D005663:Furans; C555112:caribenol A