Stereodivergent syntheses of anisomycin derivatives from D-tyrosine |
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Authors: | Kim Jin Hyo Curtis-Long Marcus J Seo Woo Duck Ryu Young Bae Yang Min Suk Park Ki Hun |
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Institution: | Department of Agricultural Chemistry, Division of Applied Life Science (BK21 programs), Gyeongsang National University, Jinju, 660-701, South Korea. |
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Abstract: | structures: see text] Enantiomerically pure 2-alkyl-3-acetoxy-4-iodopyrrolidines with all groups cis, and all adjacent groups trans (10 and 17), important precursors for the synthesis of pyrrolidinediols, have been prepared from D-tyrosine through regio- and diastereoselective reduction of a vinyl ketone and subsequent iodoamidation controlled by minimization of nonbonding steric interactions. Highly stereodivergent Woodward-Prevost methodology, applied to both iodopyrrolidines, yielded enantiomerically pure (2R,3R,4R)-, (2R,3R,4S)-, and (2R,3S,4R)-deacetylanisomycin (3, 4, and 5), each in excellent de. Incorporation of differential protection of the hydroxyl groups led to a one-pot synthesis of (2R,3R,4R)-anisomycin 2. |
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