Total synthesis of (+)-grandifloracin by iron complexation of a microbial arene oxidation product

Matthew J Palframan; Gabriele Kociok-Kohn; Simon E Lewis

doi:10.1021/ol201057r

Total synthesis of (+)-grandifloracin by iron complexation of a microbial arene oxidation product

Matthew J Palframan, Gabriele Kociok-Kohn, Simon E Lewis

Department of Chemistry

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Abstract

(+)-Grandifloracin was synthesized from sodium benzoate by means of a dearomatizing dihydroxylation that proceeds with unusual regloselectivity. 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.

Original language	English
Pages (from-to)	3150-3153
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	12
Early online date	16 May 2011
DOIs	https://doi.org/10.1021/ol201057r
Publication status	Published - 17 Jun 2011

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10.1021/ol201057r

Lewis_OrganicLetters_2011_13_12_3150.pdf
This is a copy of a Published Work that appeared in final form in Organics Letters, copyright © American Chemical Society. Reproduced here by kind permission of the ACS.
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Cite this

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Total synthesis of (+)-grandifloracin by iron complexation of a microbial arene oxidation product

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Underexploited Microbial Arene Oxidation

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Total synthesis of (+)-grandifloracin by iron complexation of a microbial arene oxidation product

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Underexploited Microbial Arene Oxidation

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