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Study on generation of conjugated heterocumulene

Research Project

Project/Area Number 12470484
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

SATO Masayuki  Professor, School of Pharmaceutical Sciences, University of Shizuoka, 薬学部, 教授 (80004654)

Co-Investigator(Kenkyū-buntansha) YUMIKO Suzuki  Research Assistant, School of Pharmaceutical Sciences, University of Shizuoka, 薬学部, 助手 (20295546)
IWAMOTO Ken-ichi  Instructor, School of Pharmaceutical Sciences, University of Shizuoka, 薬学部, 講師 (50254256)
Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 2001: ¥2,400,000 (Direct Cost: ¥2,400,000)
Keywordsheterocumulene / acyl ketene / cycloaddition / 1,3-dioxin-4-one / pyridinophane / crown ether / macrocycle / シクロファン / 熱分解 / アンサ型化合物 / ケテン / 不斉認識 / 光学分割 / 面性不斉
Research Abstract

1) A series of prochiral 2, 2-bis(hydroxylmethyl)-1, 3-dioxin-4-ones was synthesized by [4+2]cycloaddition of acylketene to protected 1, 3-dihydroxy-2-propanones followed by deprotection of the hydroxyl groups. Dissymmetrization of the prochiral dioxinones by lipase-catalyzed monoacetylation afforded optically active 2-(hydroxymethyl)dioxinones. Intramolecular photo[2+2]cycloaddition of the alkenoates of these alcohols provided an efficient method for regio-, diastereo-, and enantioselective synthesis of cyclobutanols.
2) 4-Hydroxy-2-pyrone derivative bridged by polymethylenes at the 3- and 6-positions are readily synthesized by intramolecular [4+2]cycloaddition of bis(acylketene). On heating with ammonia, the bridge 2-pyrones afforded the corresponding 2, 6-bridged 4-pyridones. This methods have a wide applicability to the bridge length; compounds with a short bridge (n = 8) as well as long bridge (n = 18) are synthesized in satisfactory yields.
3) Dehydroacetic acid derivative bridged by di(ethylene glycol) unit was synthesized by intramolecular [4+2]cycloaddition of a bis(acylketene). Heating the bridged dehydroacetic derivative with ammonia afforded crown ether type pyridinophane (12-crown-4).

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (8 results)

All Other

All Publications (8 results)

  • [Publications] 佐藤雅之, 岩本憲人: "ケテン化学の新展開"有機合成化学協会誌. 57. 76-83 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Murakami, H.Kamaya, C.Kaneko, M.Sato: "Synthesis of optically active 1,3-dioxin-4-one derivatives having Hydroxymethyl group at the 2-position and their use for regio, stereo, and enantio-selective synthesis of cyclobutanols"Tetrahedron : Asymmetry. 14. 201-215 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Sato, T.Oda, K.Iwamoto, E.Murakami: "Highly efficient methods for metacyclophane synthesis"Tetrahedron. 59(in press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Sato, T.Oda, K.Iwamoto, S.Fujii: "A new method for synthesis of crown ether type pyridinophanes"Heterocycles. 60(in press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Sato., K.Iwamoto.: "Development in ketene chemistry"J. Synth. Org. Chem. Japan. 57. 76-83 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Murakami., H.Kamaya., C.Kaneko., M.Sato.: "Synthesis of Optically Active 1, 3-Dioxin-4-one Derivatives Having Hydroxymethyl Group at the 2-Position and Their Use for Regio-, Diastereo-, and Enantioselective Synthesis of Substituted Cyclobutanols"Tetrahedron: Asymmetry. 14. 201-215 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Sato., T.Oda., K.Iwamoto., E.Murakami.: "Highly Efficient Methods for Metacyclophane Synthesis"Tetrahedron, (in press). 59. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Sato., T.Oda., K.Iwamoto., S.Fujii.: "A new method for synthesis of crown ether type pyridnophanes"Heyerocycles, (in press). 60. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary

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Published: 2001-04-01   Modified: 2016-04-21  

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