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

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

Research output: Contribution to journalArticle

40 Citations (Scopus)
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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 languageEnglish
Pages (from-to)3150-3153
Number of pages4
JournalOrganic Letters
Volume13
Issue number12
Early online date16 May 2011
DOIs
Publication statusPublished - 17 Jun 2011

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Complexation
Iron
Sodium Benzoate
iron
Oxidation
oxidation
dienes
synthesis
products
Biological Products
sodium
configurations
grandifloracin

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Total synthesis of (+)-grandifloracin by iron complexation of a microbial arene oxidation product. / Palframan, Matthew J; Kociok-Kohn, Gabriele; Lewis, Simon E.

In: Organic Letters, Vol. 13, No. 12, 17.06.2011, p. 3150-3153.

Research output: Contribution to journalArticle

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