Last letter = First Letter, min 3 syllable word chain

ragamuffin

neoconservatism

Machiavellian

nonchalant

Transylvania :bat:

accomplish

heterosexuality

yesternoon

noninflammatory

Ypsilanti

Inexplicable

extraordinary

yellowjacket

tintinnabulation

Nostradamus

steatopygia

:astonished:

astigmatism

margarita

adventurous