Abstract
The stereocontrolled total synthesis of (±)-coriamyrtin (1) has now been completed, starting from protoanemonin and 2-methyl-1, 3-cyclopentanedione, through fifteen steps. The Wittig reaction of the ditetrahydrofuranyl ether (3) with triphenylphosphonium methylide gave the exo-methylenic compound (4), which was derived to the lactone (6) by consecutive hydrolysis, alkaline hydrolysis, and lactonization. The lactone (6) was transformed into the bromoether (8), which was subjected to allylic hydroxylation to give the allyl alcohol (10). Epoxidation of the allyl alcohol (10) provided selectively the epoxy-alcohol (11), which was derived to the mesylate (16). Elimination of the O-mesyl group gave the olefin (17). Epoxidation of 17 with m-chloroperbenzoic acid gave (±)-bromocoriamyrtin (18) and finally, reductive debromination of 18 furnished (±)-coriamyrtin (1).
