Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization.

Abstract

Asimicin (1) exhibits potent antitumor activity and comprises a central C2 -symmetric bis-tetrahydrofuran and two aliphatic side-chains, one of which terminates with (S)-methyl-2(5H)-furanone. This work reports a convergent total synthesis of 1 in 17 steps from d-gulose derivative 4. Decarbonylative radical-radial homo-coupling of α-alkoxyacyl telluride 12 a efficiently produced the C2 -symmetric core 3-SS, which was transformed into 1 through stepwise attachment of the two side-chains and functional group manipulations.