Total Synthesis and Antibacterial Investigations of 1-Hydroxyboivinianin A.

Synthetic investigations of natural products has been instrumental in the development of novel antibacterial small molecules. 1-hydroxyboivinianin A, a lactone containing phenolic bisabolane isolated from marine sediment, has reported antibacterial activity against the aquatic pathogen Vibrio harveyi. The total synthesis of 1-hydroxyboivinianin A and its enantiomer was completed in a six-step sequence in 42 % overall yield. The synthesis leveraged a key diastereoselective nucleophilic addition with chiral imidazolidinone to establish the benzylic tertiary alcohol and intramolecular Horner-Wadsworth Emmons to furnish the lactone. Both enantiomers were found to have negligible antibacterial activity against a panel of gram-positive and negative bacteria and minimal antifungal activity against phytopathogens. Investigations of a possible in vitro lactone hydrolysis to produce an inactive linear acid led to the discovery of a spontaneous cyclization, suggesting the lactone is resistant to hydrolysis and the lactone is not degrading to produce an inactive species.

A look around the West Indies: The spices of life are secondary metabolites.

Natural products possess a wide range of bioactivities with potential for therapeutic usage. While the distribution of these molecules can vary greatly there is some correlation that exists between the biodiversity of an environment and the uniqueness and concentration of natural products found in that region or area. The Caribbean and pan-Caribbean area is home to thousands of species of endemic fauna and flora providing huge potential for natural product discovery and by way, potential leads for drug development. This can especially be said for marine natural products as many of are rapidly diluted through diffusion once released and therefore are highly potent to achieve long reaching effects. This review seeks to highlight a small selection of marine natural products from the Caribbean region which possess antiproliferative, anti-inflammatory and antipathogenic properties while highlighting any synthetic efforts towards bioactive analogs.