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markdown-toc
API and CLI for generating a markdown TOC (table of contents) for a README or any markdown files. Uses Remarkable to parse markdown. Used by NASA/openmct, Prisma, Joi, Mocha, Sass, Prettier, Orbit DB, FormatJS, Raneto, hapijs/code, webpack-flow, docusaurus, release-it, ts-loader, json-server, reactfire, bunyan, husky, react-easy-state, react-snap, chakra-ui, carbon, alfresco, repolinter, Assemble, Verb, and thousands of other projects.
comment-mark does exactly what you're describing to interpolate content into a markdown file using comments as placeholders. You'll have to write a script to inject what you want though but should be straight forward. Here's an example snippet:
As for the table of contents, you can either use github-markdown-toc or markdown-toc (on npm).
As for the table of contents, you can either use github-markdown-toc or markdown-toc (on npm).