Toward the Total Synthesis of Eurifoloid A

Construction of the [5–7–7]
tricyclic core of eurifoloid
A, which contains an unusual and highly strained bicyclo[4.4.1]­undecane
ring system with trans-bridgehead, was attempted
using a type II intramolecular [5 + 2] cycloaddition reaction and
a Meinwald rearrangement reaction of the epoxide as key synthetic
steps. The reported chemistry illustrates the feasibility of constructing
the 8-epi-eurifoloid A framework by type II intramolecular
[5 + 2] cycloaddition.