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  • Title: Total synthesis of pikromycin.
    Author: Oh HS, Kang HY.
    Journal: J Org Chem; 2012 Jan 20; 77(2):1125-30. PubMed ID: 22168449.
    Abstract:
    The total synthesis of pikromycin (6), the first isolated macrolide antibiotic, was achieved. The target macrolide was retrosynthetically divided into two parts, pikronolide (6a) (aglycon) and D-desosamine. The aglycon was synthesized using key reactions such as an asymmetric aldol reaction, Yamaguchi esterification, and ring-closing metathesis. The aglycon was coupled successfully with the trichloroacetimidate derivative of D-desosamine under Lewis acidic conditions to afford pikromycin. Narbomycin (5) was also synthesized from narbonolide (5a) under identical conditions.
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