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

Organic letters (2011-05-20)
Matthew J Palframan, Gabriele Kociok-Köhn, Simon E Lewis
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.

MATERIALS
Product Number
Brand
Product Description

Supelco
Sodium benzoate, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Sodium benzoate, ReagentPlus®, 99%
Sigma-Aldrich
Sodium benzoate, BioXtra, ≥99.5%
Sigma-Aldrich
Sodium benzoate, puriss., meets analytical specification of Ph. Eur., BP, FCC, E211, 99.0-100.5% (calc. to the dried substance), powder
Sigma-Aldrich
Sodium benzoate, purum p.a., ≥99.0% (NT)