I am working on an embedded systems project and have run into an issue of the compiler being programatically embedded in the Paradigm C++ IDE. I would like to be able to aut
80186 free C compiler:
http://coding.derkeiler.com/Archive/General/comp.arch.embedded/2005-09/msg01063.html
Your best bet is probably OpenWatcom, which includes a C++ compiler. Back in the early-to-mid 90s, I believe this was the best C/C++ compiler around. It was open-sourced a few years ago.
There's a patch for GCC 4.3: New back end ia16: 16-bit Intel x86
And here's an update for it. Note that it probably doesn't work very well, for example, the updated post says: "Constructors and destructors are now supported, but for some reason they only work on the elks configuration."
This Docker container has a build of it: https://registry.hub.docker.com/u/ysangkok/ia16-gcc-rask
I didn't manage to make DOS binaries yet: How do I assemble GAS assembly and link it with the Open Watcom C library?
This google search shows a series of links for setting gcc up as a cross compiler. To get it to target something other than a standard ELF binary you can frig the output. This link discusses excluding the standard libraries and customising the output format. You may have to do some fiddling to get it to work.
As an alternative openwatcom.org has an open-source version of the Watcom C compiler, which might also be able to do what you want.