re = /<img src=".*?((\/img\/[^"]+)\/thumbs\/([^"]+))".*alt="(.*?)"[^>]*class="([^"]*popup-img[^"]*)"[^>]*>/mi
str = '<img src="http://example/img/product/name/thumbs/100/img1.jpg" alt="описание фото1" width="100" height="100" caption="false" class="popup-img" />
<img src="http://example/img/product/name/thumbs/100/img2.jpg" alt="описание фото2" width="100" height="100" caption="false" class="popup-img left" />
<img src="http://example/img/product/name/thumbs/100/img2.jpg" alt="описание фото2" width="100" height="100" caption="false" class="wrong-class left" />'
subst = '<a class="$5" href="..$2/$3" title="$4" style="background: url(\'..$1\');-webkit-background-size: cover;background-size: cover;"></a>'
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