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Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin
Author(s) -
Baidilov Daler,
Rycek Lukas,
Trant John F.,
Froese Jordan,
Murphy Brennan,
Hudlicky Tomas
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804602
Subject(s) - iodobenzene , tetrodotoxin , chemistry , dihydroxylation , toluene , stereochemistry , enantioselective synthesis , total synthesis , organic chemistry , catalysis , biology , biophysics
Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.