Work

Enantioselective Total Synthesis and Confirmation of the Absolute and Relative Stereochemistry of Streptorubin B

Year: 2010

Type: article

Abstract: The enantioselective total synthesis of the pyrrolophane natural product streptorubin B is described. Key steps in the concise route include the application of a one-pot enantioselective aldol cyclization/Wittig reaction and an anionic oxy-Cope rearrangement to forge the crucial 10-membered ring. Comparisons between CD spectra of synthetic and natural samples of streptorubin B coupled with X-ray crystallography allowed for the determination of the absolute stereochemistry of this natural product for the first time. These studies also provided unambiguous proof of the relative configuration between the butyl side chain and the bispyrrole subunit. Additional studies revealed a novel atropstereoselective Paal-Knorr pyrrole condensation and provided fundamental experimental insight into the barrier for atropisomerization of the natural product.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja109165f

Authors: Dennis X. Hu, Michael D. Clift, Kiel E. Lazarski, Regan J. Thomson

Institution: Northwestern University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Northwestern University, National Institute of General Medical Sciences

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