Total synthesis of (+)-grandifloracin by iron complexation of a microbial arene oxidation product
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Matthew J Palframan1, Gabriele Kociok-Köhn, Simon E Lewis
1Department of Chemistry, University of Bath, Bath BA2 7AY, UK.
Abstract:
(+)-Grandifloracin was synthesized from sodium benzoate by means of a dearomatizing dihydroxylation that proceeds with unusual regioselectivity. Iron diene complexes formed from the arene oxidation product permit the use of otherwise inaccessible transformations. The synthetic material was shown to be antipodal to the natural product, thus determining the absolute configuration of grandifloracin for the first time.
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