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1995 Fiscal Year Final Research Report Summary

Development of New Synthetic Methods based on Early Transition Metals

Research Project

Project/Area Number 05671770
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTokyo College of Pharmacy

Principal Investigator

HANZAWA Yuji  Tokyo College of Pharmacy, School of Pharmaceutical Science, Associate Professor, 薬学部, 助教授 (10096688)

Project Period (FY) 1993 – 1995
KeywordsEarly transition metal / Zirconocene-butene complex / Ring contraction / Steroidal side chains / Diastereoselective synthesis / Catalyst / Oxetanocin / Vinylcyclopropane
Research Abstract

In our ongoing research project on organic syntheses using early transtition metals, zirconium, vanadium, niobium etc., we have exploited enormous possibilities of low valent zirconium complex, zirconocene-butene complex, for organic synthesis. During the past term of project we established an efficient method for the preparation of optically pure carbocycles by treating vinyl sugar derivatives with zirconocene-butene complex and an application to the synthesis of bioactive molecules. We also established the construction of steroidal side chain based on the reaction of zirconocene with vinylcyclopropane, and we have also studied a short-step construction of steroidal skeleton based on the reaction of zirconocene and alkoxymethylated stirene derivatives.

  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Ito,H.: "Practical zirconium-mediated deprotective method of allyl groups." J. Org. Chem. em.58. 774-775 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito,H.: "Ziconium-mediated highly diastereoselective ring contraction of carbohydrate derivatives:Synthesis of highly functionalized,enantiomerically pure carbohydrate." J. Am. Chem. Soc,. 115. 8835-8836 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito,H.: "Zirconium-mediated ring contraction of vinylmorpholine dehvatives from α-amino acid" J. Am. Chem. Soc,. 116. 5469-5470 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] HANZAWA,Y.: "Regioselective bond cleavage of Vinylcyclopropane derivative with the"zirconocene-butene"cemplex" Tetrahedron Lett.35. 9421-9424 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito,H.: "Development of new synthetic methodology based on zirconium-mediated carbon bond-carbon forming reaction" J. Org. Syn. Chem. Japan. 52. 217-225 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito,H.: "An efficient synthesis of enanticomerically pure key intermediate of carbocyclic oxetanocin" Tetrahedron Lett.34. 7639-7640 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] HANZAWA,Y.: "Formation of carbon-carbon bonds using zirconocene-butene complex as a synthetic foal" Synlett. 299-305 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito,H.: "Generation of allylic and related organozirconiums through a highly effective ziroonium-β-alkoxide elimi naton" Tetrahedron. 51. 4507-4518 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] HANZAWA,Y.: "Unprecedented reactions of substituted styrene derivatives with zikonocene-(1-butene)Complex" Tetrahedron Lett.36. 6503-6506 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] HARADA,S.: "η^3-π Allylzirconocene derivatives:Preparation of Steroidal side chains" Tetrahedron Lett.36. 9489-9492 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito, H.: "Practical zirconium-mediated deprotective method of allyl groups." J.Org. Chem.58 (3). 774-775 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, H.: "Ziconium-mediated highly diastereoselective ring contraction of carbohydrate derivatives : Synthesis of highly functionalized, enantiomerically pure carbohydarte." J.Am. Chem. Soc.115 (19). 8835-8836 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, H.: "Ziconium-mediated ring contraction : An efficient synthesis of enantiomerically pure key intermediate of carbocyclic oxetanocin." Tetrahedron Lett.34 (47). 7639-7640 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, H.: "Ziconium-mediated ring contraction of vinylmorpholine derivatives from alpha-amino acid : An application to the synthesis of (-)-Macronecine." J.Am. Chem. Soc.116 (12). 5469-5470 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hanzawa, Y.: "Regioselective bond cleavage of vinylcyclopropane derivatives with the "zirconocene-buten" complex." Tetrahedron Lett.35 (50). 9421-9424 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, H.: "Development of new synthetic methodology based on zirconium-mediated carbon-carbon bond forming reaction." J.Org. Syn. Chem. Japan.52 (3). 217-225 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hanzawa, Y.: "Formation of carbon-carbon bonds using zirconocene-butene complex as a synthetic tool." Synlett. (4). 299-305 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, H.: "Generation of allylic and related organozirconiums through a highly effective zirconiumbeta-alkoxide elimination reaction." Tetrahedron. 51 (15). 4507-4518 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hanzawa, Y.: "Unprecedented reactions of substituted stirene derivatives with zirconocene- (1-betene) complex." Tetrahedron Lett.36 (36). 6503-6506 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Harada, S.: "eta3-pi Allylzirconocene derivatives : Preparation of steroidal side chains." Tetrahedron Lett.36 (52). 9489-9492 (1995)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1997-03-04  

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