Retrosynthesis of a cyclopropane type molecule
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.