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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804602
Subject(s) - iodobenzene , chemistry , dihydroxylation , enantioselective synthesis , toluene , sharpless asymmetric dihydroxylation , stereochemistry , tetrodotoxin , total synthesis , organic chemistry , catalysis , medicine
Abstract 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.