Last letter = First Letter, min 3 syllable word chain

Lothario

Ontario

oregano

ontological

Lambrusco

orthopedic

columbine
(the flower, not the school shooting site)

-“BB”-

election

nationalistic

cosmopolitan

nudity

yammering

Grindelwald

dishwasher

reworded

deterioration

negligent

tatterdemalion

Norwegian

nefarious