P-36 SYNTHETIC STUDIES OF CHROMOPROTEIN ANTIBIOTIC C-1027 CHROMOPHORE

DOI
  • Iida K.
    Department of Chemistry, Faculty of Science, Tohoku University
  • Ishii T.
    Department of Chemistry, Faculty of Science, Tohoku University
  • Sato I.
    Department of Chemistry, Faculty of Science, Tohoku University
  • Akahori Y.
    Department of Chemistry, Faculty of Science, Tohoku University
  • Hirama M.
    Department of Chemistry, Faculty of Science, Tohoku University

Bibliographic Information

Other Title
  • P-36 タンパク-クロモフォア複合型抗生物質C-1027の合成研究(ポスター発表の部)

Abstract

Very recently, a chromophore (1) of potent antitumor chromoprotein antibiotic, C-1027, as well as kedarcidin (2), has been disclosed to possess a highly strained bicyclo[7.3.0]dodecadiyne core structure. A strategy masking the 3-ene-1,5-diyne system 1 as 1,5-diyne 3 is a fascinating approach from the viewpoints of total synthesis and design of related DNA-cleaving molecules. We developed a general and efficient route for the 9-membered cyclic diyne system through an intramolecular acetylide addition mediated by Li(TMS)_2/CeCl_3, from a precursor such as 8 possessing a conformationally not rigid C4-C5 single bond. Futhermore, we found that the cyclic 1,5-diyne system such as bicyclo[7.3.0]dodeca-2,6-diyn-11-ene 11 undergoes an unprecedentedly facile Cope rearrangement below room temperature, although its isomeric bicyclo[7.3.0]dodeca-2,6-diyn-12- enes 21 and 23 do not. Thus, the delicate supression of Cope rearrangement of 9-membered cyclic 1,5-diyne system has been attained by a subtle remote structural change. In addition, we report stereocontrolled synthesis and the abusolute configuration of the sugar moiety.

Journal

Details 詳細情報について

  • CRID
    1390001206077500160
  • NII Article ID
    110006679350
  • DOI
    10.24496/tennenyuki.36.0_657
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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