5-Methylthebaine was obtained by treating thebaine with n-butyllithium and methylfluorosulfonate. Hetero Diels-Alder reaction of thebaine and 5-methylthebaine with trifluoroacet aldehyde afforded 14-${eta}$-(triflu-oro-2-hydroxyethyl)codeine (2) and 14-${eta}$-(trifluoro-2-hydroxyethyl)-5-methylcodeinone (9). 6-${alpha}$-OH compound (4) was obtained by employing $CeCl_2$ and $NaBH_4$. After synthesized a derivative substituted for 3-OH (5), using boron tribromied, We synthesized a new derivative that make double bond in C-7, C-8 into epoxode (6), (10). Through inspecting an influence on structure-activity and analgetic action, we are going to examine which opiold acceptor has a selectivity.