title: An inverse electron demand Diels-Alder-based total synthesis of defucogilvocarcin V and some C-8 analogues.
abstract: A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.
authors.affiliation: Department of Chemistry, Memorial University, St. John's, Newfoundland and Labrador, A1B 3X7, Canada.
authors.forename: Penchal Reddy
authors.initials: PR
authors.lastname: Nandaluru
authors.forename: Graham J
authors.initials: GJ
authors.lastname: Bodwell
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry; D004583:Electrons; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; C047300:defucogilvocarcin V