Studies on the Chemical Constituents of Rutaceous Plants. Part LXXIII. Total Synthesis of Chelerythrine, a Benzo(c)phenanthridine Alkaloid.

Abstract

By taking advantage of our novel synthetic methods involving CsF-mediated Claisen rearrangement of an aryl propargyl ether to a 2-methylbenzolfuran and oxidative cleavage of the furan ring to a salicylaldehyde, total synthesis of chelerythrine, a benzo[c]phenanthridine alkaloid, was accomplished via the common intermediate (5) prepared through the two routes shown in Chart 3.