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Synlett 1994; 1994(6): 415-417
DOI: 10.1055/s-1994-22870
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A Synthesis of Salinomycin. Part 1. Synthesis of Key Fragments

Richard C. D. Brown* , Philip J. Kocienski
  • *Department of Chemistry, The University, Southampton, SO9 5NH, U. K.
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Publication Date:
18 September 2002 (online)

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Syntheses of the C11-C20 furan fragment 5 and the C21-C30 lactone fragment 6 en route to the polyether antibiotic salinomycin are described. Stereocontrol in the construction of 5 was accomplished via an asymmetric aldol reaction using an oxazolidinethione as a chiral auxiliary. Stereocontrol in the construction of 6 was accomplished by an asymmetric oxidation of a 1,5-diene with KMnO4 to generate 4 stereogenic centres in a single step.

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