Isometric view

I'm running into some trouble when making the isometric view.
I'll try to explain my problem.

I have an original image. It's a square 32x32 tile.
I want to rotate it and scale it down vertically for it to be able to fit into the isometric grid.
I want to keep rotating it under different angles before scaling, because I want to smooth 360 degrees turn.

The top example is what I want to happen.
The bottom example is what happens in every tool I tried out so far.

I cannot add transformations to the graphic seperately.
Scaling seems to be prioritized over rotation by default, and I have no idea how to chnage this behaviour.

I'm of course working on a solution, but what I'm trying to achieve here is way more default to process for a computer than having to render an actual 3d view.

I will resort to 3d if I cannot find a way to change this, but either way, the results will not be seen in the final game. Unless you have a slow computer.