Last letter = First Letter, min 3 syllable word chain

syndromic

contagious

systolic

canonical

legalistic

character

Radagast

turpitude

Ecclesiastes

sepulcher

Rumplestiltskin

negligent

Tricentennial

(It’s only 53 years away.)

liriope

engagement

tantalizing

geostationary

yellowing

gratinee

existentialist