Macrocylic bisbibenzyl natural products and their chemical synthesis

Nat Prod Rep. 2012 Feb;29(2):223-42. doi: 10.1039/c1np00080b. Epub 2011 Nov 16.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Bibenzyls / chemistry
  • Biological Products / chemistry*
  • Biological Products / pharmacology
  • Bryophyta / chemistry
  • Ethers, Cyclic / chemical synthesis
  • Ethers, Cyclic / pharmacology
  • Hepatophyta / chemistry
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / pharmacology
  • Molecular Structure
  • Phenols / chemistry
  • Primula / chemistry

Substances

  • Bibenzyls
  • Biological Products
  • Ethers, Cyclic
  • Macrocyclic Compounds
  • Phenols
  • riccardin C
  • lunularin