P-36 SYNTHETIC STUDIES OF CHROMOPROTEIN ANTIBIOTIC C-1027 CHROMOPHORE
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- Iida K.
- Department of Chemistry, Faculty of Science, Tohoku University
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- Ishii T.
- Department of Chemistry, Faculty of Science, Tohoku University
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- Sato I.
- Department of Chemistry, Faculty of Science, Tohoku University
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- Akahori Y.
- Department of Chemistry, Faculty of Science, Tohoku University
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- Hirama M.
- Department of Chemistry, Faculty of Science, Tohoku University
Bibliographic Information
- Other Title
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- 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
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- Symposium on the Chemistry of Natural Products, symposium papers
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Symposium on the Chemistry of Natural Products, symposium papers 36 (0), 657-664, 1994
Symposium on the Chemistry of Natural Products Steering Committee
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Details 詳細情報について
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- CRID
- 1390001206077500160
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- NII Article ID
- 110006679350
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- ISSN
- 24331856
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed