The sum total of the novels, basically ("literature"), although sometimes the comics count, too.
As far as onscreen Trek is concerned, there weren't many instances of planetary conquest or destruction. A planet left unconquered or undestroyed would still be rendered irrelevant if no starships could sail to or fro; the industries could no longer serve the overall war effort in any way.
Would convoy interception be a factor in a war that supposedly involved "fronts"? The only things being shipped along vulnerable lines would be those going to the fighting forces; without cloaks, the Jem'Hadar wouldn't be in a position to hurt the internal connections of the UFP.
In general, it doesn't seem as if the UFP would have major industrial assets on the outer fringes; colonies appear to be founded as tiny agricultural communities, and only gradually grow from that. At any point of time, the Federation would be a self-sustaining entity from the inside, with a shell of tentative colonies, and hitting that shell would not reduce the self-sustenance. Nor would hitting the outer layers of the core necessarily mean that the inner layers would become less self-sustaining, considering that each layer supposedly added its own self-sustenance eventually. Sol alone could probably keep up the fight in direct proportion to the volume remaining under its control (that is, if the Sol system is one millionth of effective UFP volume, then Earth fights back with one millionth of the economic resources, not one trillionth), rather than face a sudden drop in fighting ability when a key offworld location was lost.
Of course, the UFP no doubt trades extensively with its near and far neighbors - possibly more extensively than, say, the Romulans or the Klingons do. An explicit example is Rutia from TNG "High Ground". Severing of trade routes might have an economic effect, then. But would that be more on the wealthy UFP, or on its isolated individual trade partners?