title: Synthesis of a functionalized oxabicyclo[2.2.1]-heptene-based chemical library.
abstract: The 7-oxabicyclo[2.2.1]heptene ring system is a common structural motif in many pharmacologically interesting molecules. We recognized the potential to employ this highly oxygenated and conformationally-restricted scaffold in diversity-oriented synthesis to generate a library of non-chiral but topologically complex compounds. Herein, we report the synthesis and biological evaluation of two 96-member tricyclic libraries containing the oxabicyclo[2.2.1]heptene framework using acetal formation as the key step.
authors.affiliation: Department of Chemistry & Biochemistry, Ohio University, Athens, Ohio 45701, USA.
authors.forename: Sarah B
authors.initials: SB
authors.lastname: Luesse
authors.forename: Gregg
authors.initials: G
authors.lastname: Wells
authors.forename: Jeanne
authors.initials: J
authors.lastname: Miller
authors.forename: Erin
authors.initials: E
authors.lastname: Bolstad
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Bergmeier
authors.forename: Mark C
authors.initials: MC
authors.lastname: McMills
authors.forename: Nigel D
authors.initials: ND
authors.lastname: Priestley
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Wright
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D041221:Candida glabrata / Q000187:drug effects; D006536:Heptanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D054852:Small Molecule Libraries / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001643:Bridged Bicyclo Compounds; D006536:Heptanes; D054852:Small Molecule Libraries