A molecule of the week instead of a problem of the week, I like it! Interesting molecule (although it has too many nitrogens and not enough oxygens or stereocenters for my liking
), I don't think about this type of molecules very much though.
Looking at it at first I would think you'd want to find a quick convergent way, and cut the molecule in half somehow. I was thinking perhaps a cross-coupling of some sort, and then just an addition to form the amide. I think the stereocenter would be pretty tricky to install, ethyl vs methyl (although I think I've seen some recent organocatalytic reactions that can proceed with high ee's), but when I searched to find the basics about this molecule, it shows a hydroxyl. Is the stereocenter supposed to be an ethyl back and a hydroxyl group up?