Last letter = First Letter, min 3 syllable word chain

silliness

supersaturating

gestation

nonchalance

elemental

liposuction

neocortex

xenophobic

contraindication

nomenclature

Eliza

acrimonious

semidocumentary

yesteryear

rapscallion

neoclassicist

trombonist

Tamborine

entrepreneurial

ladronism