title: Stereoselective synthesis of functionalised carbocyclic amides: construction of the syn-(4aS,10bS)-phenanthridone skeleton.
abstract: A new synthetic approach has been developed for the preparation of 7-deoxypancratistatin analogues bearing a syn-(4aS,10bS)-phenanthridone ring junction. A one-pot tandem process involving a substrate-directed Overman rearrangement and ring closing metathesis reaction was developed for the stereoselective synthesis of a carbocyclic allylic trichloroacetamide. Conversion to a 6-bromopiperonyl amide, followed by a Heck reaction generated a homoallylic alcohol and completed the syn-(4aS,10bS)-phenanthridone carbon skeleton. Stereoselective epoxidation and dihydroxylation of the syn-(4aS,10bS)-phenanthridone framework was then investigated leading to the preparation of new analogues of 7-deoxypancratistatin.
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, Glasgow, UK.
authors.forename: Sajjad
authors.initials: S
authors.lastname: Ahmad
authors.forename: Michael D
authors.initials: MD
authors.lastname: Swift
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Farrugia
authors.forename: Hans Martin
authors.initials: HM
authors.lastname: Senn
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010616:Phenanthrenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D004852:Epoxy Compounds; D010616:Phenanthrenes; C040601:phenanthridone