An efficient construction of bicyclic systems containing a seven-membered ring by tandem ring-closing metathesis reactions of dienynes

Various (5–7) and (6–7) bicyclic dienes bearing quaternary methyl group and ester functionality have been synthesized from acyclic dienynes by tandem ring-closing metathesis (RCM) reaction. Epoxidation of these conjugated dienes led to bicyclic vinyl oxiranes which undergo acid-catalyzed addition of alcohols to afford highly oxygenated compounds.

Graphical abstractA series of (5–7) and (6–7) bicyclic dienes bearing quaternary methyl group and ester functionality have been synthesized from acyclic dienynes by tandem ring-closing metathesis (RCM) reaction. Epoxidation of these conjugated dienes followed by methanolysis of the resulting oxiranes led to highly oxygenated compounds.Figure optionsDownload full-size imageDownload as PowerPoint slide