Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization

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...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-12, Vol.24 (71), p.18907-18912
Main Authors: Kawamata, Takahiro, Yamaguchi, Akinori, Nagatomo, Masanori, Inoue, Masayuki
Format: Article
Language:English
Subjects:
Aliphatic compounds
Anticancer properties
Antitumor activity
Chains
Chemistry
Convergence
Dimerization
Functional groups
Intermetallic compounds
natural products
radical reactions
Synthesis
Tellurides
tellurium
Tetrahydrofuran
total synthesis
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Summary: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. A convergent total synthesis of the potent antitumor agent asimicin in 17 steps from a d‐gulose derivative is reported. Decarbonylative radical‐radial homo‐coupling of α‐alkoxyacyl telluride efficiently produced the central C2‐symmetric bis‐tetrahydrofuran substructure, which was transformed into asimicin through stepwise attachment of the two aliphatic side‐chains.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805317