title: Total synthesis of eupomatilones 4 and 6: structurally rearranged and atropisomerically fluxional lignan natural products.
abstract: [structure: see text] A convergent and diastereocontrolled total synthesis of eupomatilones 4 and 6 is reported and was based on a diastereoselective hydroboration/oxidation sequence and a convergent Lipshutz biarylcuprate cross-coupling reaction. The structure of eupomatilone 6 is revised.
authors.affiliation: Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA. coleman@chemistry.ohio-state.edu
authors.forename: Robert S
authors.initials: RS
authors.lastname: Coleman
authors.forename: Srinivas Reddy
authors.initials: SR
authors.lastname: Gurrala
mesh_terms: D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis*; D003432:Cross-Linking Reagents / Q000737:chemistry; D003500:Cyclization; D017705:Lignans / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D003432:Cross-Linking Reagents; D017705:Lignans; C502383:eupomatilone 4; C485126:eupomatilone-6