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Synlett 1990; 1990(6): 323-325
DOI: 10.1055/s-1990-21078
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Total Synthesis of Avermectin B1a: Planning of the Synthesis and Preparation of the C1-C10 "Southern" Hydrobenzofuran Fragment

Alan Armstrong* , Steven V. Ley
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London, SW7 2AY, England
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Publication Date:
08 March 2002 (online)

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A strategy for the synthesis of the anthelmintic macrolide avermectin B1a (1) is presented, involving a highly convergent approach necessitating the preparation and coupling of five key fragments. The C1-C10 hydrobenzofuran unit 2 was obtained in 14 steps from a previously reported, optically pure cyclohexanone derivative 3.