Total Synthesis of (±)-Jujuyane

The first total synthesis of (+/-)-jujuyane, a cyclo-octanoid natural product, was accomplished from a (5 + 3) dimerization product of oxidopyrylium ylide that forms the cyclooctanoid core structure along with inherited stereochemical bias. Selective functional group modifications of the highly oxygenated dimeric structure, followed by the tactical functional group manipulation around the eight-membered carbocyclic core, enabled the total synthesis of (+/-)-jujuyane, which will serve a guide for future applications of oxidopyrylium dimers to the natural product total synthesis.

Automated summary

The first total synthesis of (+/-)-jujuyane was achieved from a (5 + 3) dimerization product of oxidopyrylium ylide, which established the cyclooctanoid core structure with stereochemical bias. Selective functional group modifications of the dimeric structure, followed by strategic functional group manipulations around the eight-membered carbocyclic core, paved the way for the total synthesis of (+/-)-jujuyane and will guide future applications in natural product synthesis using oxidopyrylium dimers.