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Published on: April 19, 2019
Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization
Takahiro Kawamata1, Akinori Yamaguchi1, Masanori Nagatomo1
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-003, Japan.
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.
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