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Synthesis of optically active ferrocene-containing platensimycin derivatives with a C6–C7 substitution pattern


Patra, Malay; Gasser, Gilles; Wenzel, Michaela; Merz, Klaus; Bandow, Julia E; Metzler-Nolte, Nils (2011). Synthesis of optically active ferrocene-containing platensimycin derivatives with a C6–C7 substitution pattern. European Journal of Inorganic Chemistry, 2011(22):3295-3302.

Abstract

Concurrently with the emergence of purely organic derivatives of the naturally occurring antibiotic platensimycin (1a), herein, we describe the design, synthesis and biological evaluation of both the enantiomers of a C6–C7 ferrocene-fused platensimycin derivative 2b. (S,SP)- and (R,RP)-2b were prepared in nine steps starting from commercially available 4-ferrocenyl-4-oxobutyric acid via highly diastereoselective Michael additions of optically active planar-chiral ferrocene-fused cyclohexanone derivatives (5) with acrylate ester as the key step. Manual superimposition of (S,SP)-2b on platensimycin bound to the active site of its target enzyme FabF suggests that the former fits nicely in the active site and the C6–C7-fused ferrocene occupies a pocket similarly to the C8–C9-fused tetracyclic cage of 1a. Antimicrobial activities of (S,SP)- and (R,RP)-2b were tested against various Gram-positive and Gram-negative bacterial strains.

Abstract

Concurrently with the emergence of purely organic derivatives of the naturally occurring antibiotic platensimycin (1a), herein, we describe the design, synthesis and biological evaluation of both the enantiomers of a C6–C7 ferrocene-fused platensimycin derivative 2b. (S,SP)- and (R,RP)-2b were prepared in nine steps starting from commercially available 4-ferrocenyl-4-oxobutyric acid via highly diastereoselective Michael additions of optically active planar-chiral ferrocene-fused cyclohexanone derivatives (5) with acrylate ester as the key step. Manual superimposition of (S,SP)-2b on platensimycin bound to the active site of its target enzyme FabF suggests that the former fits nicely in the active site and the C6–C7-fused ferrocene occupies a pocket similarly to the C8–C9-fused tetracyclic cage of 1a. Antimicrobial activities of (S,SP)- and (R,RP)-2b were tested against various Gram-positive and Gram-negative bacterial strains.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2011
Deposited On:21 Mar 2012 14:22
Last Modified:05 Apr 2016 15:41
Publisher:Wiley-Blackwell
ISSN:1434-1948
Publisher DOI:https://doi.org/10.1002/ejic.201100497

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