Unmasking the 6,7,5-tricarbocyclic frame of
Opening of the bridging ether of 8-oxabicyclo[3.2.1]oct-6-ene systems 1,7-fused to a five-membered carbocycle that bears a double bond conjugated to that of the oxabicycle can be induced at low temperaure by the addition of an organolithium reagent. If this double bond is unsubstituted, the opening occurs via an anti-1,6-addition pathway, and if substituted it takes place by means of a more classical syn SN2' addition.
Rodriguez
JR
Departamento de Quimica Organica, Universidad de Santiago de Compostela, Spain.
Castedo
L
Mascarenas
JL