title: Cyclopentitol as a scaffold for a natural product-like compound library for drug discovery.
abstract: A concise and efficient synthesis of cyclopentitols as a scaffold for a two-dimensional compound library for drug discovery is described. Starting from d-mannose, the key steps are Wittig olefination and ring-closing metathesis (RCM) followed by a [3,3]-sigmatropic Overmann rearrangement to form an sp(3)-rich, natural product-like scaffold from which a focused compound library with different functionalities is prepared.
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, PO Box 9502, Universiteit Leiden, 2300 RA Leiden, The Netherlands.
authors.forename: Jalindar D
authors.initials: JD
authors.lastname: Padwal
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, PO Box 9502, Universiteit Leiden, 2300 RA Leiden, The Netherlands.
authors.forename: Dmitri V
authors.initials: DV
authors.lastname: Filippov
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, PO Box 9502, Universiteit Leiden, 2300 RA Leiden, The Netherlands.
authors.forename: Bharat D
authors.initials: BD
authors.lastname: Narhe
authors.affiliation: Mercachem, Kerkenbos 1013, 6546 BB Nijmegen, The Netherlands.
authors.forename: Sjoerd
authors.initials: S
authors.lastname: Aertssen
authors.affiliation: Mercachem, Kerkenbos 1013, 6546 BB Nijmegen, The Netherlands.
authors.forename: Remmelt Jan
authors.initials: RJ
authors.lastname: Beuving
authors.affiliation: Mercachem, Kerkenbos 1013, 6546 BB Nijmegen, The Netherlands.
authors.forename: Jorg C J
authors.initials: JC
authors.lastname: Benningshof
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, PO Box 9502, Universiteit Leiden, 2300 RA Leiden, The Netherlands.
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, PO Box 9502, Universiteit Leiden, 2300 RA Leiden, The Netherlands.
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, PO Box 9502, Universiteit Leiden, 2300 RA Leiden, The Netherlands. Electronic address: m.van.der.stelt@chem.leidenuniv.nl.
authors.forename: Mario
authors.initials: M
authors.lastname: van der Stelt
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D055808:Drug Discovery; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D010429:Pentoses / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis*
chemical_list: D001688:Biological Products; D010429:Pentoses; D011083:Polycyclic Compounds; D054852:Small Molecule Libraries; D008358:Mannose
keywords: Cyclopentitols; Drug discovery; Focused library; Natural product-like compounds