title: Combining the Petasis 3-component reaction with multiple modes of cyclization: a build/couple/pair strategy for the synthesis of densely functionalized small molecules.
abstract: A build/couple/pair strategy for the synthesis of complex and densely functionalized small molecules is presented. The strategy relies on synthetically tractable building blocks (build), that is, diversely substituted hydrazides, α-hydroxy aldehydes, and boronic acids, which undergo Petasis 3-component reactions (couple) to afford densely functionalized anti-hydrazido alcohols. The resulting scaffolds can subsequently be converted via chemoselective cyclization reactions (pair), including intramolecular Diels-Alder or Ru-alkylidene catalyzed ring-closing metathesis, into sets of structurally diverse heterocycles in good yields in only 3-4 steps.
authors.affiliation: Department of Chemistry, Technical University of Denmark , DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Thomas
authors.initials: T
authors.lastname: Flagstad
authors.forename: Mette R
authors.initials: MR
authors.lastname: Hansen
authors.forename: Sebastian T
authors.initials: ST
authors.lastname: Le Quement
authors.forename: Michael
authors.initials: M
authors.lastname: Givskov
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Nielsen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D003500:Cyclization
chemical_list: D000447:Aldehydes; D001386:Azides; D001897:Boronic Acids
keywords: Petasis 3-component reaction; build/couple/pair; diversity-oriented synthesis; intramolecular Diels−Alder reaction; ring-closing metathesis