How do I match a filename without quotes to a name with quotes? - regex

Question

If somebody knows a better title, please do tell me.
Given these examples:
Three files called: Jacobs.Ladder.txt, Emma.Unplugged.2020.txt & Emma.txt
Three folders called: Jacobs.Ladder.2019, Emma.Unplugged & Emma
Three database-entries called: Jacob's Ladder, Emma: Unplugged & Emma
My PowerShell script is presented with the file, then needs to find the right folder, copy it there, then find the entry in the database and update it there. I need a script that catches all three cases.
So far, what I've done is this:
I take the file's BaseName property:
Jacobs.Ladder, Emma.Unplugged, Emma
I use Get-ChildItem to put all directories in a variable, do:
$Directories | Where-Object -Property 'Name' -Contains $File.BaseName
This finds exact matches, so it will only find the folder Emma
Next, if nothing was found, I do:
$Directories | Where-Object -Property 'Name' -Like ('{0}*' -f $File.BaseName)
This finds the folder Jacobs.Ladder.2019. It has already found Emma in the previous step, so that has been handled. It will not however, find Emma.Unplugged because the file's BaseName is Emma.Unplugged.2020.
So that's my first challenge/question: how do I write a conditional that matches Emma.Unplugged.2020 to Emma.Unplugged?
Next, to match the file name with the database entries, I start with a replace to turn the dots into spaces.
I then search for an almost exact match:
$Database | Where-Object -Property 'Name' -Like $FileNameWithSpaces.Replace(' ','*')
I know, I could have just replaced the dots with asterisks. But I don't know yet if the name with spaces is going to be useful somewhere else.
Although this does compensate for the colon in Emma.Unplugged, this once again only finds Emma.
There is my second challenge: how do I form my query to match (again) Emma.Unplugged.2020 to Emma: Unplugged but also Jacobs.Ladder to Jacob's Ladder?
Of course, if you can think of more scenarios that I didn't catch here, feel free to add those in your code.
As for the topic title, my biggest challenge is that single quote in the word. Right now the best way I can think of is if I on-the-fly turn all database-names into their filename equivalent. Then Jacob's Ladder would become Jacobs.Ladder and I would have a match. Which would leave the 2020 as my biggest challenge.