Work

Development of a Merged Conjugate Addition/Oxidative Coupling Sequence. Application to the Enantioselective Total Synthesis of Metacycloprodigiosin and Prodigiosin R1

Year: 2009

Type: article

Abstract: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja906122g

Authors: Michael D. Clift, Regan J. Thomson

Institution: Northwestern University

Language: English

Topic: Synthesis and Characterization of Pyrroles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: New Methods for the Concise Synthesis of Bioactive Polycyclic Molecules