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)
書誌事項
- タイトル別名
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- P-36 SYNTHETIC STUDIES OF CHROMOPROTEIN ANTIBIOTIC C-1027 CHROMOPHORE
抄録
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.
収録刊行物
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 36 (0), 657-664, 1994
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390001206077500160
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- NII論文ID
- 110006679350
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可