title: Macrocylic bisbibenzyl natural products and their chemical synthesis.
abstract: Covering: 1995 to June 2011. The macrocyclic bisbibenzyl family of natural products are commonly found in liverworts and other bryophytes, though the recent isolation of riccardin C from a primrose extract has demonstrated their existence in higher flowering plants. Each has a core comprising four aromatic rings and two ethano bridges, being derived in Nature from two molecules of lunularin. Sub-classes are distinguished by the connectivity between these lunularin units, while individual natural products are distinguished by the hydroxy- and/or alkoxy-substituents decorating the core structures. Further diversification results from halogenation and oxidation, which may lead to dimerization or the creation of additional rings. The review provides a timely update to a previous Natural Product Reports article by Keseru and Nógrádi (Nat. Prod. Rep. 1995, 12, 69-75) and largely focuses on new additions to the family and the strategies used to effect their chemical synthesis.
authors.affiliation: Chemistry, University of Southampton, Southampton, SO17 1BJ, UK. dch2@soton.ac.uk
authors.forename: David C
authors.initials: DC
authors.lastname: Harrowven
authors.forename: Sarah L
authors.initials: SL
authors.lastname: Kostiuk
mesh_terms: D001632:Bibenzyls / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry* / Q000494:pharmacology; D044002:Bryophyta / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000494:pharmacology; D035926:Hepatophyta / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D031825:Primula / Q000737:chemistry
chemical_list: D001632:Bibenzyls; D001688:Biological Products; D004988:Ethers, Cyclic; D047028:Macrocyclic Compounds; D010636:Phenols; C505660:riccardin C; C121619:lunularin