I've known a couple of people. One drove a motor home from Amsterdam to Saudi, over 25 years ago and one who attempted it from Bahrain to the UK about 15 years ago in a Clapped out (circa 1960s) Jeep clone from Japan which made it as far as Egypt before it fell appart.
If you are a westerner, I suspect you will have a lot of trouble in getting visas and permission in going through Saudi, Jordan and Syria. And even more problems in actually crossing the borders.