19 強力な免疫抑制作用を持つマイカラミドAの合成研究(口頭発表の部)

DOI

書誌事項

タイトル別名
  • 19 Synthetic Studies toward the Total Synthesis of Strong Immunosuppressive Agent Mycalamide A

抄録

Mycalamide A was originally isolated from a New Zealand marine sponge in 1988. Mycalanide A exhibits immunosuppressive activity by suppressing T-cell more effectively than FK506. In addition, mycalamide A possesses a quite unique structure bearing a tetrahydropyran ring and a trioxadecalin ring system bridged by an N-acyl aminal bond, therefore mycalamide A has attracted much attention of synthetic organic chemists. Despite the availability of many synthetic routes for mycalamide A, there still exists a need to develop strategies more efficient than those currently in existence. As a result of our ongoing studies on natural product synthesis, we became interested in developing a novel synthetic route for the synthesis of mycalamide family. (I) Development of a novel δ-lactone synthesis In order to prepare the left segment 7 of mycalamide A, a unique one-pot nucleophilic substitution-lactonization process was created using cyclopropane derivative B and a phenyl selenide. This technique was applied to the corresponding cyclopropane alcohol, derived from 5, providing δ-lactone 6 in good yield. (II) Development of a unique catalytic system in cross-aldol reactions For stereoselective construction of the right segment 12 of mycalamide A, a novel catalytic system, Yb(OTf)_3-TMSCl, was devised using a cyclohexanone and a ketene silyl acetal as a model case. The desired aldol products 9 was obtained as a single stereoisomer employing the above methodology. (III) Total synthesis of mycalamide A A total synthesis of mycalamide A has been achieved by coupling left segment 7 and right segment 12 followed by functional group manipulations.

収録刊行物

詳細情報

  • CRID
    1390001206078788736
  • NII論文ID
    110006682526
  • DOI
    10.24496/tennenyuki.47.0_107
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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