re = /((?s)(\[)(\d)(\])([ ])(?=.*:LOOKUP\3=(\w+))|(\[(\d+)\])[ ])((?<artist1>Frank Sinatra)?(\s-\s)(?<title1>.*)(?<ext1>\..*)|(?<title2>.*)(\s-\s)(?<artist2>Frank Sinatra)(?<ext2>\..*)|(?<title3>.*)(?<ext3>\..*))|(?<dict>RegExDictionary:.*)$/mi
str = '[8] Frank Sinatra - One For My Friend.flac
[51] Come Fly With Me - Frank Sinatra.dsf
[2] Frank Sinatra - Love Me Tender.flac
[17] New York, New York.mp3
[45] Singing In The Rain - Frank Sinatra.flac
RegExDictionary:LOOKUP0=00:LOOKUP1=01:LOOKUP2=02:LOOKUP3=03:LOOKUP4=04:LOOKUP5=05:LOOKUP6=06:LOOKUP7=07:LOOKUP8=08:LOOKUP9=09'
subst = '$6$8${title1}${title2}${title3}${ext1}${ext2}${ext3}'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html