It was concluded that biological activity is dependent upon an optimal conformation defined by a narrowly fixed angle between the planes of the C6-indole and the tetracyclic unit.
Requiring five reactions starting from indole, all of which are reasonably high yielding, this is an effective method for synthesizing yeuhchukene.
This method aims to build the entire molecule in one step by exploiting the fact that yuehchukene has been characterized as the structurally unusual dimer of β-(dehydroprenyl)indole.
[7][8] Under acidic conditions a Diels-Alder reaction of β-(dehydroprenyl)indole can produce yuehchukene.
This is due to the alcohol precursor dehydrating under acidic conditions to produce both the diene and dienophile required for this reaction.
Requiring only three reactions, this method is shorter than the previous route but the yields of the final step are quite poor.