Synthesis of (±)-Waihoensene
Total Synthesis of (±)-Waihoensene.
Angew. Chem. Int. Ed. 2017;
18 August 2017 (online)
Isolated from a New Zealand podocarp in 1997, waihoensene is a tetracyclic diterpene with four contiguous quaternary carbon centers. Lee and co-workers report the first total synthesis of the title compound by employing a trimethylenemethane cycloaddition.
Condensation of aldehyde F with tosylhydrazide followed by elimination, afforded diazoalkane G, which underwent the key tandem cycloaddition to afford tetracycle J. Four more steps completed the synthesis of (±)-waihoensene.