Parse-tree paths are commonly used to incorporate information from syntactic parses into NLP systems. These systems typically treat the paths as atomic (or nearly atomic) features; these features are quite sparse due to the immense variety of syntactic expression. In this paper, we propose a general method for learning how to iteratively simplify a sentence, thus decomposing complicated syntax into small, easy-to-process pieces. Our method applies a series of hand-written transformation rules corresponding to basic syntactic patterns — for example, one rule “depassivizes” a sentence. .