Off the top of my head, you could try a Heck coupling between iodobenzene and methylenecyclopentane.
That would give you Ph-CH=cyclopentane
Treating with mCPBA would convert the double bond to an epoxide.
typically, Heck reactions tend to occur with electron deficient alkenes (like enoates, enones, styrenes etc unless they are in an intramolecular sense). but thats a clever idea and this rule is not completely restrictive.
If you are looking to begin with 6-carbons or less, you might want to consider what kinds of reactions aromatic systems undergo to build complexity. I agree with pacifyer and Cancer Boy that your best bet would be to consider construction of the epoxide from the corresponding alkene. with this in mind, you have a starting point and a step before the finishing step. how can you connect those two to suggest a synthesis?