Asymmetric Synthesis via Acetal Templates. 14. Preparation of Enantiomerically Pure (3S,4S)- and (3S,4R)-Statine Derivatives |
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Authors: | R G Andrew R E Conrow J D Elliott W S Johnson S Ramezani |
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Institution: | Department of Chemistry, Stanford University, Stanford, California 94305, U.S.A. |
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Abstract: | Several (3S,4S)- and (3S,4R)-statine derivatives have been prepared by attack of nucleophiles on crystalline, epimeric N-BOC-lactams 7a and 7b. The key step in the synthesis of the lactams was the TiCl4-catalyzed coupling reactions of acetals derived from (R)-1,3-butanediol with allyltrimethylsilane. Several enantiometrically pure (3S,4S- and (3S, 4R)-statine derivatives were made by sodium cyanide-catalyzed reaction of nucleophiles with the lactams 3a and 3b which were synthesized by the scheme 1 → 2 → 3. |
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