Last letter = First Letter, min 3 syllable word chain

Caribbean

narcotic

chocolaty

youthfulness

simplistic

complexity

yellowtail

landlubber

Rolodex

Xylophil

(brand-name of a medical ointment containing 5% lidocaine)

-“BB”-

laryngitis

salient

theater

reticent

transmission

Novocaine

Enfamil

lactation

nurtural

laceration