title: Access to a Structurally Complex Compound Collection via Ring Distortion of the Alkaloid Sinomenine.
abstract: Many compound collections used in high-throughput screening are composed of members whose structural complexity is considerably lower than that of natural products. We previously reported a strategy for the synthesis of complex and diverse small molecules from natural products using ring-distortion reactions, called complexity-to-diversity (CtD), and herein, CtD is applied in the synthesis of 16 diverse scaffolds and 65 total compounds from the alkaloid natural product sinomenine. Chemoinformatic analysis shows that these compounds possess complex ring systems and marked three-dimensionality.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
authors.forename: Alfredo
authors.initials: A
authors.lastname: Garcia
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
authors.forename: Bryon S
authors.initials: BS
authors.lastname: Drown
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Hergenrother
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D015195:Drug Design; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry* / Q000302:isolation & purification; D032841:Sinomenium / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009019:Morphinans; D054852:Small Molecule Libraries; C009271:sinomenine