re = /(?x) # Free-Spacing
(?(DEFINE) # Define a few subroutines
(?<double>“(?:(?!&[lr]squo;).)*”) # full set of doubles (no quotes inside)
(?<single>‘(?:(?!&[lr]dquo;).)*’) # full set of singles (no quotes inside)
(?<notquotes>(?:(?!&[lr][sd]quo;).)*) # chars that are not quotes
) # end DEFINE
^ # Start of string
( # Start group: balanced portion
(?: # Start non-capture group
(?¬quotes) # Any non-quote chars
&l(?<type>[sd])quo; # Opening quote, capture single or double type
# any full singles, doubles, not quotes or recursion
(?:(?&single)|(?&double)|(?¬quotes)|(?R))*
&r\k<type>quo; # Closing quote of the correct type
)*+ # Repeat non-capture group
) # end balanced portion
\K
(
(?¬quotes)
&r([sd])quo; # unmatched quote
)/
str = '“Full Quote” The Left Quote is Missing”
'
subst = '&l\\7quo;\\6'
result = str.sub(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