Development of Highly Stereoselective Reactions Based on Tricarbonyl (η<SUP>6</SUP>-o-trimethylsilylbenzaldehyde)-chromium (0) Complex

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Other Title
  • (o-トリメチルシリルベンズアルデヒド)クロム錯体を活用する高立体選択的反応の開発
  • o トリメチルシリルベンズアルデヒド クロム サクタイ オ カツヨウスル コウ
  • Development of Highly Stereoselective Reactions Based on Tricarbonyl (&eta;<SUP>6</SUP>-o-trimethylsilylbenzaldehyde)-chromium (0) Complex

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Description

Treatment of the tricarbonyl (η6-o-trimethylsilylbenzaldehyde) chromium (0) complex with cyclic silyl enol ether species under the Mukaiyama condition resulted in highly stereoselective formation of syn-aldol products, whereas the aldol reaction with O-silyl ketene O, S-acetals afforded the corresponding antiproducts in a highly stereoselective manner. The tricarbonyl (η6-o-trimethylsilylbenzaldehyde) chromium (0) complex has also emerged as an excellent substrate for highly regio-and stereoselective construction of cis-3, 5-isoxazolidine derivatives in the 1, 3-dipolar cycloaddition reaction. By taking advantage of our newly developed aldol reaction, we have succeeded in highly stereocontrolled syntheses of some biologically active compounds such as C-13 side chains of taxol and taxotere, the N-terminal amino acid of nikkomycin B and Bx, and antitumor styryllactones : goniofufurone, goniotriol, and goniothalenol.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 114 (7), 478-491, 1994

    The Pharmaceutical Society of Japan

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