title: Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".
abstract: A concise, nine-step enantioselective total synthesis of metacycloprodigiosin is reported. The synthesis provides increased step-efficiency over the previous racemic and enantioselective syntheses of this compound. Key features of the work include investigations into a convergent oxidative coupling reaction and subsequent ring-closing metathesis to deliver an advanced pyrrole intermediate we name the "Wasserman pyrrole" that can be converted to metacycloprodigiosin in one step.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208.
authors.forename: Marvin M
authors.initials: MM
authors.lastname: Vega
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208.
authors.forename: Diana M
authors.initials: DM
authors.lastname: Crain
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208.
authors.forename: Leah C
authors.initials: LC
authors.lastname: Konkol
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208.
authors.forename: Regan J
authors.initials: RJ
authors.lastname: Thomson
keywords: Metacycloprodigiosin; Oxidative coupling; Prodigiosin alkaloids; Ring-closing metathesis