My diesel experiance is limited, but I loved my 79 diesel rabbit...
Years ago when diesel was cool for like a month I believe it was oldsmobile that tried to refit their gas engines to run on diesel to capture the "emerging market" It was a boondogle, they took gas engines and reinforced them for higher compression, and a few other things, but the big problem was that the reinforcement was not enough and the higher compression tore the engine apart in short order. That being said I think a small two stroke might work.
Here is my thinking on it...I believe the compression issue increases geometrically, not linear so as the engine gets bigger the forces and higher compression ratio multiplies instead of adds, (I could be wrong, but it sounds good) Plus a smaller engine may be able to take more stress than a larger displacement because a 1/4 inch of steel is porportianal greater when lining a 50cc chamber as opposed to a 100cc chamber.(numbers are off but you see my theory, again I could be wrong). So by the above theories the engine might handle the higher compression....maybe....If the HT can take and produce a low end 15:1 ratio
If they engine could handle the compression the rest is cake. The glow plugs are just needed to start the engine, once it gets going the compression alone keeps the motor going. So in theory on a hot summer day might not even need the glow plugs...
The problem I see with diesel in a HT two stroke is the injector. Gas vaporizes pretty easy, suck it through a carb with a slight vacuum and you have your mix. Diesel needs to be "pushed" through an injector. How are you going to power the injector/pump? Spark timing is a non issue, but injector timing would be critical.
So put an injector where the spark plug belongs, close the intake port, and figure out your pump and away you go...I almost think it is doable....