Synthesis and biological evaluation of cleistocaltone A, an inhibitor of respiratory syncytial virus (RSV)

The first chemical synthesis of the phloroglucinol meroterpenoid cleistocaltone A (1) is presented. This compound, previously isolated from Cleistocalyx operculatus was reported to show promising antiviral properties. Based on a modified biosynthesis proposal, a synthetic strategy was devised featuring an intramolecular Diels-Alder reaction and an epoxidation/elimination sequence to generate the allyl alcohol handle in the side chain. The strategy was successfully executed and synthetic cleistcaltone A was evaluated against a contemporary RSV-A strain.