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gcc-ia16
Fork of Lambertsen & Jenner (& al.)'s IA-16 (Intel 16-bit x86) port of GNU compilers ― added far pointers & more • use https://github.com/tkchia/build-ia16 to build • Ubuntu binaries at https://launchpad.net/%7Etkchia/+archive/ubuntu/build-ia16/ • DJGPP/MS-DOS binaries at https://gitlab.com/tkchia/build-ia16/-/releases • mirror of https://gitlab.com/tkchia/gcc-ia16
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WorkOS
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There is a more recent fork of gcc/DJGPP to make 16-bit DOS applications that I also never tried, but that might be worth using (and I think it is bundled in the latest FreeDOS, so it might be very easy to set up by just installing that in a virtual machine?): https://github.com/tkchia/gcc-ia16
Reading: https://github.com/jagregory/abrash-black-book
There's a script for building a DJGPP cross compiler: https://github.com/andrewwutw/build-djgpp