Retrosynthesis of a cyclopropane type molecule I'm trying to work out a retrosynthesis of the following molecule:



The issue I'm having is regarding the building up of the carbon skeleton. I know I can build the cyclopropane group using a carbene (diiodomethane, zinc) on the alkene. However, the alkene is proving difficult to build, I can't see why an obvious way around building this (Witting/from the equivalent alkyne) wouldn't work here. Is there something I am missing here like a rearrangement?
How about this? Cyclopropane from carbene + maleic anhydride. Add 2 eq methyl Grignard and trap with methyl iodide.

Possibly, you could do the exhaustive addition of Grignard first, then cyclopropanate and methylate in one shot with diazomethane. Thanks to Beerhunter for this suggestion in comments.