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Synfacts 2010(3): 0261-0261  
DOI: 10.1055/s-0029-1219245
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 6-Deoxyerythronolide B

Contributor(s): Steven V. Ley, Catherine F. Carter
E. M. Stang, M. C. White*
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

6-Deoxyerythronolide B contains a highly functionalized core that is common in polyketide macrolide antibiotics. C-H oxidative macrocyclization is achieved here at a late stage of the synthetic sequence. The oxidation protocol is step 19 of a 22-step sequence that furnished the desired natural product in 7.8% overall yield.