Total synthesis of eupomatilones 4 and 6: structurally rearranged and atropisomerically fluxional lignan natural products.
[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.
Coleman
Robert S
RS
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA. coleman@chemistry.ohio-state.edu
Gurrala
Srinivas Reddy
SR
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
D001572:Benzofurans; D003432:Cross-Linking Reagents; D017705:Lignans; C502383:eupomatilone 4; C485126:eupomatilone-6