Synthesis of L-carbafuranomycin, an unnatural analogue of the antibiotic amino acid furanomycin.
[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.
Lee
Ja Young
JY
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany.
Schiffer
Guido
G
Jäger
Volker
V
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001412:Bacillus subtilis / Q000187:drug effects; D002384:Catalysis; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
D000596:Amino Acids; D000900:Anti-Bacterial Agents; C508394:L-carbafuranomycin; C063753:furanomycin