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Synthesis 2000; 2000(3): 395-398
DOI: 10.1055/s-2000-6343
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Synthesis of C1-C6 Segment of Carbonolide B: Wolff Rearrangement of Sugar α-Diazo Ketones

Jayant N. Tilekar* , Nitin T. Patil, Dilip D. Dhavale
  • *Garware Research Centre, Department of Chemistry, University of Pune, Pune - 411 007, India; E-mail: ddd@chem.unipune.ernet.in
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Publikationsdatum:
31. Dezember 2000 (online)

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Silver benzoate catalysed Wolff rearrangement of a series of α-diazo ketones, derived from furanuronic acids, in methanol proceeds with good yields to produce the corresponding one carbon homologated methyl-5-deoxy-hexo-furanuronate. The utility of methyl-1,2-O-isopropylidene-3-O-methyl-5-deoxy-α-d-xylo-hexo-furanuronate was demonstrated in the synthesis of the right wing segment of carbonolide B - the aglycone of the 16 membered macrolide antibiotic carbomycin B.

α-diazo ketones - Wolff rearrangement - macrolide antibiotics - carbomycin - carbonolide