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Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization
Author(s) -
Kawamata Takahiro,
Yamaguchi Akinori,
Nagatomo Masanori,
Inoue Masayuki
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805317
Subject(s) - tetrahydrofuran , convergent synthesis , derivative (finance) , total synthesis , chemistry , side chain , stereochemistry , anomer , core (optical fiber) , materials science , organic chemistry , solvent , financial economics , economics , polymer , composite material
Asimicin ( 1 ) exhibits potent antitumor activity and comprises a central C 2 ‐symmetric bis‐tetrahydrofuran and two aliphatic side‐chains, one of which terminates with ( S )‐methyl‐2(5 H )‐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 C 2 ‐symmetric core 3‐ SS , which was transformed into 1 through stepwise attachment of the two side‐chains and functional group manipulations.