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Synthetic Studies of Reveromycin A : An Inhibitor of Eukaryotic Cell Growth

Research Project

Project/Area Number 12672082
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionRIKEN (The Institute of Physical and Chemical Reseach)

Principal Investigator

SHIMIZU Takeshi  RIKEN(The Institute of Physical and Chemical Reseach), Synthetic Organic Chemistry Laboratory, Senior Scientist, 有機合成化学研究室, 副主任研究員 (80087569)

Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2001: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2000: ¥2,500,000 (Direct Cost: ¥2,500,000)
Keywordsreveromycin A / inhibitor of eukaryotic cell growth / inhibitor of protein synthesis / anti-tumor agent / 6, 6-spiroacetal / asymmetric total synthesis / succinylation / reaction under high pressure / 6,6-スピロケタール / Julia olefination
Research Abstract

Reveromybin A is a novel polyketide-type antibiotic produced by Steptomyces sp. and inhibits mitogenic activity induced by the epidennal growth factor in a mouse epidermal keratinocyte. The characteristic structural features of reveromycin A include a 1, 7-dioxaspiro[5.5]undecane moiety, that is, the 6, 6-splroacetal system bearing a hemisuccinate, two alkenyl carboxylic acids, and methyl and n.-butyl groups. The first total synthesis of reveromycin A has been designed and accomplished. Our synthesis is based on the stereoselective and convergent synthesis of the 6, 6-spiroacetal system followed by the succinylation of tertiary alcohol under high pressure and the installation of the polyene-containing side chains. We also studied the syntheses and activities of reveromycin A derivatives.

Report

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

    (6 results)

All Other

All Publications (6 results)

  • [Publications] T.Shimizu: "Total Synthesis of Reveromycin A"Organic Lett.. 2. 2153-2156 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Shimizu: "Succinylation of Tertiary Alcohols under High Pressure"Synthesis. 1027-1034 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Ebihara M: "Kanki Publishing Company"Genetic manipulations. 223. 2156-2000 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Shimizu, T. ; Hiramoto, K. ; Nakata, T: "Succinylation of Tertiay Alcohols under High Pressure"1027. 1034-2001

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Shimizu: "Succinylalion of Tertiary Alcohols under High Pressure"Synthesis. 1027-1034 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Shimizu,T.,Masuda,T.,Hiramoto,K.,Nakata,T: "Total Synthesis of Reveromysin A"Organic Letters. 2 . 2153-2156 (2000)

    • Related Report
      2000 Annual Research Report

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

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