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. 2008 Sep 19;73(18):7420-3.
doi: 10.1021/jo801294p. Epub 2008 Aug 13.

Synthesis of carbapyochelins via diastereoselective azidation of 5-(ethoxycarbonyl)methylproline derivatives

Wathsala Liyanage  1 , Laksiri Weerasinghe, Roland K Strong, Juan R Del Valle
Affiliations

Synthesis of carbapyochelins via diastereoselective azidation of 5-(ethoxycarbonyl)methylproline derivatives

Wathsala Liyanage et al. J Org Chem. .

Abstract

Two configurationally stable carbon-based analogues of pyochelin have been prepared from Boc-pyroglutamic acid-tert-butyl ester in 11 and 13 steps. Introduction of the amino group was achieved by a highly diastereoselective electrophilic azidation reaction to afford novel bis-alpha-amino acid proline derivatives.

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Figures

Figure 1
Figure 1
Pyochelin and configurationally stable proline-based analogues.
Scheme 1
Scheme 1
Attempted C–H Insertion Route
Scheme 2
Scheme 2
Electrophillic Azidation Reactions
Figure 2
Figure 2
Proposed transition state models for the electrophilic azidation of 10.
Scheme 3
Scheme 3
Synthesis of Carbapyochelins 2 and 3
Scheme 4
Scheme 4
Synthesis and X-ray Structure of 16
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