New Chiral Synthons from Glcidol and their Applications to Natural Products Synthesis.

• Project/Area Number: 04640533
• Research Category: Grant-in-Aid for General Scientific Research (C)
• Allocation Type: Single-year Grants
• Research Field: 天然物有機化学
• Research Institution: Kwansei Gakuin University
• Principal Investigator: KATSUMURA Shigeo Kwansei Gakuin University Chemistry Professor, 理学部, 教授 (70047364)
• Project Period (FY): 1992 – 1993
• Project Status: Completed (Fiscal Year 1993)
• Budget Amount: ¥2,100,000 (Direct Cost: ¥2,100,000); Fiscal Year 1993: ¥600,000 (Direct Cost: ¥600,000); Fiscal Year 1992: ¥1,500,000 (Direct Cost: ¥1,500,000)
• Keywords: (R)-Glycidol / Threoninol / Hydroxyphenylalaninol / Sphingoshine / Phospholipase A2 / Stereoselectiv Synthesis / New lnhibitor / Oxazoline Phospholipid / 両異性体 / キラル補助剤 / 不斉アルドール反応 / グリシドール / オキサゾリジノン誘導体 / キラルな合成シントン / ホスホリパーゼA_2阻害 / リン脂質類縁体

Research Abstract

Syntheses of all stereoisomers of threoninol and hydroxyphenylalaninol from (R)-glycidol via an oxazolidinone derivative werer established. As a further application, stereoselective synthesis of sphinfoshine wes realized. A new phospholipase A2 inhibtitor, oxazolidinone phospholipid was also synthesized.

Research Products

• [Publications] S.Katsumura: "Synthesis of Oxazoridinone Phospholipid Analogue As a New Inhibitor of Phospholipase A_2" Bioorganic & Medicinal Chemistry Letters. 3. 2703-2706 (1993)
  • Description: 「研究成果報告書概要(和文)」より
• [Publications] S.Katsumura: "Diastereoselective Synthesis of γ-Hydroxy-β-amino Alcohols,Threoninol and Hydroxyphenylalaninol from(R)-Glycidol" Tetrahedron:Asymmetry. 5. 161-164 (1994)
  • Description: 「研究成果報告書概要(和文)」より
• [Publications] S.Katsumura: "Stereoselective Synthesis of L(-)-Threo and D(+)-Erythro Sphingosines from(R)-Glycidol" Chemistry Letters. (to be submitted).
  • Description: 「研究成果報告書概要(和文)」より
• [Publications] S.Iwama: "A New Inhibitor of Phospholipase A2:Synthesis and Inhibition Mechanism of Oxazolidinone Phospholipid" Tetrahedron. (to be submitted).
  • Description: 「研究成果報告書概要(和文)」より
• [Publications] S.Iwama: "A New Route for Protected Amino Alcohols from(R)-Glycidol" Bull.Chem.Soc.Jpn.(to be submitted).
  • Description: 「研究成果報告書概要(和文)」より
• [Publications] S.Katsumura: "Synthesis of Oxazoridinone Phospholipid Analogue As a New lnhibitor of Phospholipase A2" Bioorganic & Medicinal Chemistry Letters. 3. 2703-2706 (1993)
  • Description: 「研究成果報告書概要(欧文)」より
• [Publications] S.Katsumura: "Diastereoselective Synthesis of g-Hydroxy-b-amino Alcohols, Threoninol and Hydroxyphenylalaninol from (R)-Glycidol" Tetrahedron : Asymmetry. 5. 161-164 (1994)
  • Description: 「研究成果報告書概要(欧文)」より
• [Publications] S.Katsumura: "Stereoselective Synthesis of L(-)-Threo and D(+)-Erythro Sphingosines from (R)-Glycidol" Chemistry Letters. (to be submitted.).
  • Description: 「研究成果報告書概要(欧文)」より
• [Publications] S.Iwama: "A New Inhibitor of Phosholipase A2" Synthesis and Inhibition Mechanism of Oxazolidinone Phospholipid, Tetrahedron. (to be submitted.).
  • Description: 「研究成果報告書概要(欧文)」より
• [Publications] S.Iwama: "A New Route for Protected Amino Alcohols from (R)-Glycidol" Bull. Chem. Soc. Jpn.(to be submitted.).
  • Description: 「研究成果報告書概要(欧文)」より
• [Publications] S.Katsumura: "Synthesis of Oxazoridinone Phospholipid Analogue As a New lnhibitor of Phodpholipase A_2" Bioorganic&Medicinal Chemistry Letters. 3. 2703-2706 (1993)
• [Publications] S.Katsumura: "Diastereoselective Synthesis of gamma-Hydroxy-beta-amino Alcohols,(2S,3S)-and(2S,3R)-Threoninol and-Hydroxyphenylalaninol,from(R)-Glycidol" Tetrahedron:Asymmetry. 5,(in press). (1994)