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  • Title: Synthesis of L-carbafuranomycin, an unnatural analogue of the antibiotic amino acid furanomycin.
    Author: Lee JY, Schiffer G, Jäger V.
    Journal: Org Lett; 2005 Jun 09; 7(12):2317-20. PubMed ID: 15932187.
    Abstract:
    [reaction: see text] L-(+)-carbafuranomycin is a novel analogue of L-(+)-furanomycin, an unusual antibiotic alpha-amino acid that attracted great interest due to its activity as an isoleucine antagonist. We present here a concise and efficient asymmetric synthesis of this carba-analogue starting with the 1,3-dipolar cycloaddition of a chiral nitrile oxide with cyclopentadiene. Notably, the methyl group was introduced by an S(N)2' cuprate substitution with high stereo- and regioselectivity.
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