Total synthesis of pikromycin |
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Authors: | Oh Hong-Se Kang Han-Young |
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Affiliation: | Department of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Korea. |
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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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