Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1.
A merged conjugate addition/oxidative coupling sequence that represents an efficient strategy for preparing structurally diverse pyrroles has been developed. Success of the method hinged upon the controlled oxidative coupling of unsymmetrical silyl bis-enol ether intermediates, formed by the 1,4-addition of a Grignard reagent with subsequent enolate trapping by a (chloro)silylenol ether. The process was applied to the first enantioselective syntheses of the biologically active pyrrolophane natural products, metacycloprodigiosin and prodigiosin R1.
Clift
Michael D
MD
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Thomson
Regan J
RJ
D010084:Oxidation-Reduction; D011353:Prodigiosin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
C098402:metacycloprodigiosin; C531541:prodigiosin R1; D011353:Prodigiosin