Complex sentence: Filippo satisfied his father with enough academic achievement that he was allowed to take a job with a painter named Mango, but deprived of his brother, Benedetto became despondent and was eventually allowed to work at Mango's.
Split into simpler sentences: Filippo satisfied his father with enough academic achievement that he was allowed to take a job with a painter named Mango. Deprived of his brother, Benedetto became despondent and was eventually allowed to work at Mango's.