9 光学活性シクロペンタノンを原料とする数種の生理活性化合物の合成(口頭発表の部)

DOI

書誌事項

タイトル別名
  • 9 Synthesis of Biologically Active Compounds Utilizing Chiral cyclopentanones

抄録

Chiral cyclopentane derivatives have widely been employed as important starting materials in the syntheses of naturally occurring compounds. Development of an efficient preparation of a chiral cyclopentane derivative from readly available substances with both (+)- and (-)-forms is therefore desirable. We have established an efficient procedure for the preparation of chiral 2-isopropeny1-5-methyl-4-oxocyclo-pentane-1-carboxylate(1) and (2), whose substituents would be transformed into variety of functional groups, from readily avairable (-)- and (+)-carvone. First, the (-)-isomer(1) was employed in the synthesis of (+)-tecomanine (7), an antipodal form of hypoglycemic monoterpene alkaloid, where the aminylium ion-induced cyclization played an important role. Whereas, N-acetyl-L-acosamine (32), found as a structural component of glycosidic antibiotic, was also derived from the (+)-isomer (2) by utilizing the Beckmann rearrangement and Baeyer-Villiger oxidation as key reactions. Finally, Melillo's lactone(34), a key intermediate for the synthesis of carbapenem antibiotic (+)-thienamycin, was prepared from (-)-isomer(1) by manipulation of its substituents in reasonably high-yield.

収録刊行物

詳細情報 詳細情報について

  • CRID
    1390001206073328128
  • NII論文ID
    110006678621
  • DOI
    10.24496/tennenyuki.29.0_63
  • 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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