Curious if this the list below represents what you're trying to achieve
It uses a JS/JSON approach and is based on the entries you provided. It
assumes the indentations were tabs and returns them as tabs.
In this case it looks like the synonyms (curly braces) sort to the bottom,
after all alpha-numeric characters.
Putting them above should be a relatively simple tweak.
*ambition {ambitious}ancientancient civilizationapex {#1} {number
1}appetizingapprehendapproach {approaching}approachableapproval
{approve}
{approving}egoeleganceelegantemailembarrassmentembryonicemergenceemotion
affection devotion fondness love passion
sympathy tenderness warmth agitated flustered
frantic {agitation} amusement {amused} {amusing}
{emotional}
{emotions}empathyemphasisenchantmentencouragementendingenduranceenergyenhancementenjoymentennuienthusiasmenvyequalitytrain*
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