Automated synthesis has been going on since the 1980's with the biggest bottlenecks being high yields at every step to minimize purification. It's possible to build many building blocks with existing technologies but the conformational space will be limited by the available chemistry and/or the software needed to design flexible structures that thermodynamically adopt the desired conformation. Overall, I vote for better software to direct synthesis. Right now you almost always have to pair a computational chemist with an organic chemist to get a molecular design that is actually likely capable of being synthesized and will, maybe, have the properties you want.
Martin