Remarkable selectivity in addition of alcohols to epoxydienes of 5,7 bicyclic and 5,7,6 tricyclic systems

F.-D. Boyer (1) , Issam Hanna (2)

1 Unité de phytopharmacie et médiateurs chimiques
2 DCSO - Laboratoire de synthèse organique

(Chemical Equation Presented) Acid-catalyzed addition of alcohols to tricyclic dienyl epoxides such as 4 or bicyclic vinyl oxiranes such as 17 exclusively occurred at the vinyl terminus of unsaturated system through a typical SN2' process affording 1,6- and 1,4-dioxygenated derivatives, respectively.

Keywords: +/--GUANACASTEPENE- A; VINYL EPOXIDES; HYDROAZULENE PORTION; FORMAL SYNTHESIS; CARBON SKELETON; RING SYSTEMS; ALKYLATIONS; CORE; CONSTRUCTION; 5,7 BICYCLIC SYSTEMS; 5,7,6 TRICYCLIC SYSTEMS

Keywords: EPOXYDIENES

Domains: Food engineering; Chemical and Process Engineering

F.-D. Boyer, Issam Hanna. Remarkable selectivity in addition of alcohols to epoxydienes of 5,7 bicyclic and 5,7,6 tricyclic systems. Journal of Organic Chemistry, 2005, 70 (3), pp.1077-1080. ⟨10.1021/jo0481295⟩. ⟨hal-00954807⟩