Here's a different approach using a simplification rule for "if" expressions. The unsolved part here is to detect discontinuities and generate delta functions for those locations. If you want to ignore those, you can define FOO
to return 0. Note that I didn't attempt to implement the function discontinuities
; that part is unsolved here. I can give it a try if there is interest.
(%i1) display2d : false $
(%i2) matchdeclare ([aa, bb, cc], all, xx, symbolp) $
(%i3) 'diff (if aa then bb else cc, xx) $
(%i4) tellsimpafter (''%, apply ("if", [aa, diff (bb, xx), true, diff (cc, xx)]) + FOO (aa, bb, cc, xx)) $
(%i5) FOO (a, b, c, x) := 'lsum ((ev (c, x = d) - ev (b, x = d)) * delta (d, x), d, discontinuities (a, x)) $
(%i6) diff (if x > 0 then x^2 else x^3, x);
(%o6) (if x > 0 then 2*x else 3*x^2)+'lsum((d^3-d^2)*delta(d,x),d,
discontinuities(x > 0,x))