title: Polymer supported synthesis of a natural product-inspired oxepane library.
abstract: Natural product inspired compound collections are prevalidated due to the evolutionary selection of the natural product scaffolds. Their synthesis requires the development of novel strategies amenable to formats suitable for library build-up. We describe a method for the synthesis of an oxepane library inspired by the core structure of oxepane natural products endowed with multiple bioactivities. Core aspects of the strategy are the establishment of a one-pot method employing different immobilized scavengers, the employment of an enyne ring closing reaction and diversification by means of different transformations, for example, cycloadditions and cross-metathesis reactions. In total, a collection of 115 oxepanes was obtained in 5-6-step reaction sequences.
authors.affiliation: Max-Planck-Institut für molekulare Physiologie, Otto-Hahn Strasse 11, 44227 Dortmund, Germany; Technische Universität Dortmund, Fachbereich Chemische Biologie, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.
authors.forename: Sudipta
authors.initials: S
authors.lastname: Basu
authors.affiliation: Max-Planck-Institut für molekulare Physiologie, Otto-Hahn Strasse 11, 44227 Dortmund, Germany; Technische Universität Dortmund, Fachbereich Chemische Biologie, Otto-Hahn-Str. 6, 44227 Dortmund, Germany. Electronic address: herbert.waldmann@mpi-dortmund.mpg.de.
authors.forename: Herbert
authors.initials: H
authors.lastname: Waldmann
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011108:Polymers / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D006571:Heterocyclic Compounds; D011108:Polymers; D054852:Small Molecule Libraries
keywords: Cross-metathesis reaction; Cycloaddition; Enyne ring closing reaction; Immobilized scavengers; One-pot synthesis; Oxepane; Polymer supported synthesis