title: Synthesis of novel molecular probes inspired by harringtonolide.
abstract: A novel harringtonolide-inspired scaffold containing a cycloheptatriene ring and two fused cyclopentane rings has been synthesised from simple starting materials. The scaffold, containing a similar substitution pattern and relative stereochemistry to the complex diterpenoid, has been enumerated into a small library of derivatives. One of these library members has been converted into a sub-library of substituted triazoles using copper-catalysed azide-alkyne cycloaddition (click) chemistry. The scaffold may be useful in drug discovery or in the preparation of additional molecular probes for chemical biology.
authors.affiliation: Eskitis Institute, Griffith University, Nathan, QLD 4111, Australia.
authors.forename: Vinayak
authors.initials: V
authors.lastname: Hegde
authors.forename: Marc
authors.initials: M
authors.lastname: Campitelli
authors.forename: Ronald J
authors.initials: RJ
authors.lastname: Quinn
authors.forename: David
authors.initials: D
authors.lastname: Camp
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D055808:Drug Discovery; D006248:Harringtonines / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015335:Molecular Probes / Q000032:analysis / Q000138:chemical synthesis*; D009369:Neoplasms / Q000188:drug therapy; D010946:Plants, Medicinal / Q000737:chemistry; D054852:Small Molecule Libraries / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism; D032490:Taxaceae / Q000737:chemistry*; D014230:Triazoles / Q000032:analysis / Q000138:chemical synthesis*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D001386:Azides; D003517:Cyclopentanes; D006248:Harringtonines; D015335:Molecular Probes; D054852:Small Molecule Libraries; D014230:Triazoles; D003300:Copper