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Synthesis of C_2- symmetric α, α'-disubstituted azacycloalkanes as chiral building blocks and their application

Research Project

Project/Area Number 12672050
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTohoku Pharmaceutical University (2001-2002)
Toyama Medical and Pharmaceutical University (2000)

Principal Investigator

TAKAHATA Hiroki  Professor, 薬学部, 教授 (00109109)

Co-Investigator(Kenkyū-buntansha) OUCHI Hidekazu  Research Associate, 薬学部, 助手 (30275606)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 2002: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2001: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2000: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywordsdouble asymmetric allylboration / C_2 symmetrically chiral building block / alkaloid / asymmetric synthesis / substituted piperidine / 置換ピロリジン / 二重不斉アリルホウ素化 / ピペリジン / ピロリジン / C_2対称 / キラル素子 / インドリチジン
Research Abstract

Recently, C_2 symmetric chiral compounds have been recognized as chiral auxiliary and chiral building block. Therefore, considerable effort has been directed toward synthesizing them. It is known double asymmetric reaction of achiral symmetric and bifunctionalized substrate provided C_2 symmetric chiral compounds accompanied with enantiomeric enhancements. We explored a novel C_2 symmetric 2, 6-diallylpiperidine as a chiral building block via the double asymmetric allylboration of 1, 6-heptadiene followed by aminocyclization and carbamation. Its synthetic utility has been demonstrated in the expedient synthesis of piperidine-related alkaloids such as of 2, 6-trans-dialkylpiperidines such as (-)-epi-dihydropinidine, a constituent of pine and spruce species, and (2R, 6R)-trans-solenopsin A, a constituent of fire-ant venom, precoccinelline, a ladybug defense alkaloid, and (-) porantheridine, a novel tricyclic alkaloid of Poranthera corymbosa, based on distinctive desymmetrization using iodocarbamation as a key step, along with the protection of one allyl group. Further application of this procedure to other alkaloids such as (-)-lythrandine is currently under investigation.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] Takahata, H., Ouchi, H., Ichinose, M., Nemoto, H.: "A novel C2-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester as a promising chiral building block for piperidine-related alkaloids"Organic Letters. 4. 3459-3462 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Takahata, H.; Ouchi, H.; Ichinose, M.; Nemoto, H.: "A novel C_2-symmetric 2, 6-diallylpiperidine carboxylic acid methyl ester as a promising chiral building block for piperidine-related alkaloids"Organic Letters. 4(20). 3459-3462 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Takahata, H, Ouchi, H, Ichinose, M, Nemoto, H.: "A novel C2-symmetric 2,6-diallypiperidine carboxylic acid methyl ester as a promising chiral building block for piperidine-related alkaloids"Organic Letters. 4・20. 3459-3462 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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