Может быть что-то вроде:
import time
trg_arr = [ ('/var/www/html/wordpress/hyosyo/001.pdf', 'Thu Nov 20 18:07:52 2019') \
, ('/var/www/html/wordpress/hyosyo/008.pdf', 'Thu Nov 7 18:08:24 2019') \
, ('/var/www/html/wordpress/hyosyo/221.pdf', 'Thu Nov 7 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/222.pdf', 'Thu Nov 8 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/223.pdf', 'Thu Nov 9 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/224.pdf', 'Thu Nov 10 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/225.pdf', 'Thu Nov 11 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/226.pdf', 'Thu Nov 12 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/227.pdf', 'Thu Nov 13 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/228.pdf', 'Thu Nov 14 18:10:10 2019') \
, ('/var/www/html/wordpress/hyosyo/401.pdf', 'Fri Nov 8 09:00:39 2019')]
sorted_arr = sorted(trg_arr, key=lambda e: time.strptime(e[1]), reverse=True)
last_five = sorted_arr[:5]
print('Target list:')
print(trg_arr)
print('Sorted list:')
print(sorted_arr)
print('Last five:')
print(last_five)