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Studies toward the Asymmetric Synthesis of Azasugars

Research Project

Project/Area Number 10650846
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionShizuoka University

Principal Investigator

TAKABE Kunihiko  Shizuoka University, Faculty of Engineering, Professor, 工学部, 教授 (30022239)

Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 1999: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1998: ¥2,300,000 (Direct Cost: ¥2,300,000)
KeywordsAzasugar / Imide / Asymmetric synthesis / Biologically active alkaloid / Enzymatic reaction / Azetidine / Pyrrolidine / Piperidine / 酵素的不斉識別 / 位置選択的還元 / Grignard試薬付加 / キラルイミド誘導体
Research Abstract

The azasugars such as polyhydroxy azetidines, pyrrolidines and piperidines, are a unique class of natural products isolated from various plant, bacteria and other organisms which exhibit potent in anti-HIV activity and antitumor activity.
The target molecule of azasugars in this project are Jatropham (1) (antitumor activity), Azaribose (2) (antagonist activity), BM-1 (3) (bifidobacterium division-promoting activity), Isofagomine (4) (glucosidase inhibitory activity), and natural pyrrolidine alkaloids, Broussonetine C (5) and Lentiginosine (6).
The key step in our route to (1) incorporates a highly regioselective reduction of citraconimide followed by a lipase-catalyzed kinetic resolution. An asymmetric approach towards (2) is based on a strategy of enzymatic differentiation of the symmetrical dihydroxysuccimides. The synthesis of (3) is accomplished by the effective oxidation of the corresponding hydroxyazetidine. The approach to the synthesis of (4) involves the lipase-catalyzed asymmetric induction of 1,3-propanediol derivatives and. the stereoselective dihydroxylation of the unsaturated piperidin-2-one. The key part of the synthesis of (5) and (6) is the nucleophilic addition of Grignard reagent to tataric C2-imide followed by the stereoselective deoxgenation by EtィイD23ィエD2SiH.
We developed a new, practical, methodology for the total synthesis of (1), (3), (5), and (6).

Report

(3 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] N.Mase: "First synthesis of (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one(jatropham)by lipase-catalyzed kinetic resolution"Tetrahedron ; Asymmetry. 10. 4469-4471 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Yoda: "Asymmetric synthesis of tetrasubstituted tetrahydrofuran,2-epi-goniothalesdiol,employing stereoselective hydrogenation"Synlett.. 12. 1969-1971 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Yoda: "First total syntesis of a new tetrasubstituted pyrrolidine alkaloid,Broussonetine C"Tetrahedron Letters. 40. 1335-1336 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Yoda: "Novel asymmetric synthesis of an indolizidine alkaloid,(+)-lentiginosine employing highly stereoselective hydrogenation"Synlett.. 2. 137-138 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Yoda, M. Kawauchi, and K. Takabe: "Novel asymmetric synthesis of an Indolizidine Alkaloid, (+)-Lentiginosine Employing Highly Stereoselective Hydrogenation of a-Hydroxypyrrolidine"Synlett.. (2). 137-138 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Yoda, T. Shimojo, and K. Takabe: "First Total Synthesis of a New Tetrasubstituted Pyrrolidine Alkaloid, Broussonetine C"Tetrahedron Lett.. 40(7). 1335-1336 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Yoda, T. Shimojo, and K. Takabe: "Asymmetric Synthesis of Tetrasubstituted Tetrahydrofuran, 2-Epigoniothalesdiol, Employing Stereoselective Hydrogenation"Synlett.. (12). 1969-1971 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N. Mase, T. Nishi, Y. Takamori, H. Yoda, and K. Takabe: "First Synthesis of (R)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) by lipase-catalyzed kinetic resolution"Tetrahedron: Asymmetry. 10. 4469-4471 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N.Mase: "First synthesis of (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one(jatropham) by lipase-catalyzed kinetic resolution"Tetrahedron;Asymmetry. 10. 4469-4471 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Yoda: "First total synthesis of Tetrasubstituted Tetrahydrofuran Lignan,(-)-Virgatusin"Tetrahedron Letters. 40. 4701-4702 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Yoda: "First total synthesis of a new tetrasubstituted pyrrolidine alkaloid, Broussonetine C"Tetrahedron Letters. 40. 1335-1336 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Yoda: "Novel asymmetric synthesis of an indolizidine alkaloid (+)-Lentiginosine" Synlett.(2). 137-138 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H.Yoda: "Stereoselective synthesis of tetrasubstituted furan from dihidoroxyacetone-dimer" Synlett.(8). 855-856 (1998)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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