Improved Syntheses of Morinol C and D by Employing Mizoroki-Heck Reaction and Their Cytotoxic and Antimicrobial Activities

Abstract

Improved syntheses of optically pure (−)- and (+)-morinol C, and (−)- and (+)-morinol D were achieved by employing the Mizoroki-Heck reaction to construct the cinnamyl moiety. The protective group of the alkene substrate affected the yield of this key reaction. The reaction with a combination of the acetate-protected olefin and 4-methoxyphenylboronic acid gave the best result producing morinol C and D. All stereoisomers of morinol C and D showed cytotoxic activity, with (R,R)-morinol C showing the highest antibacterial activity.