The shine from the sun will stop where something blocks it: the car, the hands of the clock (maybe), the jogging figure. Not the plane since its shadow will be cast away from the ground if the clock is the sun and is the source of the light. So your shadows will start wherever there is an object between the clock and the viewer.
Since you are using single point perspective and the sun/clock is at the same point as the perspective convergence you already have a big clue as to where the shadows will fall. The light rays will be following the same path as the perspective lines, the distortion of the perspective is not a problem as the shadows will flow along the same distorted lines.
edit: You mention that it will be black and white pen art but doesn't matter if you are using pen and ink or graphite or paint, the shadows will start and lay in the same place. Also, even though you are only using black marks on a white page, you can still introduce tone through line weight, texture, and pattern.