• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

1999 Fiscal Year Final Research Report Summary

Preparation and Exploitation of Versatile Cycloalkanoid Chiral Building Blocks

Research Project

Project/Area Number 09470479
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

OGASAWARA Kunio  Organic Chemistry, Tohoku University, Professor, 大学院・薬学研究科, 教授 (60004602)

Co-Investigator(Kenkyū-buntansha) TAKAHASHI Michiyasu  Organic Chemistry, Tohoku University, Research Associate, 大学院・薬学研究科, 教務職員 (80089789)
TANIGUCHI Takahiko  Organic Chemistry, Tohoku University, Research Instructor, 大学院・薬学研究科, 助手 (90271915)
SUGAHARA Tsutomu  Organic Chemistry, Tohoku University, Research Instructor, 大学院・薬学研究科, 助手 (50006350)
Project Period (FY) 1997 – 1999
Keywordschiral building block / enzymatic synthesis / lipase / asymmetric synthesis / enantiomerization / enantiocontrolled synthesis / diastereocontrolled synthesis / natural product synthesis
Research Abstract

Two cycloalkanoid chiral building blocks, one serving as the synthetic equivalent of chiral cyclopentadienone and the other serving as the synthetic equivalent of chiral cyclohexadienone, have been prepared in enantiomerically pure forms in both enantiomeric forms by employing either enzymatic or catalytic enantioselective reaction. Both of the building blocks carry a common bicyclo[2.2.1]octane background in their molecules which serve as the protecting group for one of the enone olefin functionality. At the same time, this protecting group brings about molecular bias allowing diastereocontrolled modification of the other enone moiety of both of the chiral building blocks and may be removed under thermolysis conditions to regenerate the olefin protected by extrusion of cyclopentadiene through a retro-Diels-Alder reaction.
A variety of biologically active natural products, more than fifty, were synthesized enantio- and diastereo-controlled mannor from these building blocks by employing a variety of reactions, such as Claisen rearrangement, [2,3]-Witting rearrangement, tandem-Diels-Alder-ene reaction, Diels-Alder reaction, Fischer indolization, Bailis-Hillman reaction, Heck and Sonogashira reactions, etc, which occurred diastereoselectively from the convex-face of the chiral building blocks owing to the biased-framework of the chiral building blocks.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Hiroyuki Konno: "An Enantio-and Diastereoselective Synthesis of(-)-Isoretronecanol and(+)-Trachelanthamidine from a Meso Precursor"Heterocycles. 49. 33-37 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsutomu Sugahara: "Bailis-Hillman Protocol in an Enantiocontrolled Synthesis of Pentenomycin I"Synlett. 419-420 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kou Hiroya: "Preparation of the Synthetic Equivalents of Chiral Cyclohexadienone and Cycloheptadienone : The Enantio-and Diastereo-controlled Synthesis of(-)-Clavularin B"Synlett. 529-532 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Konno: "Practical Preparation of Versatile Chiral Building Blocks"Synthesis. 1135-1140 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiromi Nakashima: "A Stereocontrolled Route to(-)-Epibatidine Using a Chiral cis-Cyclohexadiene-1,4-diol Equivalent"Synlett. 1405-1406 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kou Hiroya: "The first enantiocontrolled synthesis of naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates(-)-zeylenol, (-)-uvarigranol G"Chem.Commun.. 390-391 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Konno: "An Enantio- and Diastereoselective Synthesis of (-)-Isoretronecanol and (+)-Trachelanthamidine from a Meso Precursor"Heterocycles. 49. 33-37 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Sugahara: "Baillis-Hillman Protocol in an Enantiocontrolled Synthesis of Pentenomycin I"Synlett. 419-420 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kou Hiroya: "Preparation of the Synthetic Equivalents of Chiral Cyclohexadienone and Cycloheptadienone : The Enantio- and Diastereo-controlled Synthesis of (-)-Clavularin B"Synlett. 529-532 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Konno: "Practical Preparation of Versatile Chiral Building Blocks"Synthesis. 1135-1140 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiromi Nakashima: "A Stereocontrolled Route to (-)-Epibatidine Using a Chiral cis-Cyclohexadine-1,4-diol Equivalent"Synlett. 1405-1406 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kou Hiroya: "The first enantiocontrolled synthesis of naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates (-)-zeylenol, (-)-uvarigranol G, (-)-tonkinenin A and (+) pipoxide"Chem. Commun.. 391-9931 (1999)

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

URL: 

Published: 2001-10-23  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi