title: Cascade polyketide and polyene cyclizations: biomimetic total synthesis of hongoquercin B.
abstract: The total synthesis of hongoquercin B was carried out in 9 steps from trans,trans-farnesyl acetate using a palladium catalyzed decarboxylative π-farnesyl rearrangement of a diketo-dioxinone ester, aromatization and cationic diene-epoxide cyclization as key steps. This cascade tetracyclization simplifies the synthesis of terpenoid resorcylate natural products.
authors.affiliation: Department of Chemistry, Imperial College London , London SW7 2AZ, England.
authors.forename: Tim N
authors.initials: TN
authors.lastname: Barrett
authors.forename: Anthony G M
authors.initials: AG
authors.lastname: Barrett
mesh_terms: D003500:Cyclization; D008968:Molecular Conformation; D011090:Polyenes / Q000737:chemistry*; D061065:Polyketides / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011090:Polyenes; D061065:Polyketides; D012717:Sesquiterpenes; C114156:hongoquercin B