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

François-Didier Boyer (1) , Issam Hanna (2)

1 Unité de Phytopharmacie et Médiateurs Chimiques, INRA, Versailles, France
2 DCSO - Laboratoire de synthèse organique

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. © 2006 Elsevier B.V. All rights reserved.

Domains: Organic chemistry

François-Didier Boyer, Issam Hanna. An efficient construction of bicyclic systems containing a seven-membered ring by tandem ring-closing metathesis reactions of dienynes. Journal of Organometallic Chemistry, 2006, 691 (24-25), pp.5181-5188. ⟨10.1016/j.jorganchem.2006.07.014⟩. ⟨hal-00951296⟩