P-27 非環式エンイン-アレンを経由するビラジカル生成モデルの合成(ポスター発表の部)
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Esperamicins and related antibiotics possessing the characteristic cis-hex-3-ene-1,5-diynyl group have attracted considerable attention due to the generation of a phenylene biradical which is responsible for DNA strand scission. Designing the structurally simplified enediyne congeners retaining the impressive DNA cleaving properties is of great importance for potential use for chemotherapy or as tools for biotechnology. Ongoing research concerned with the development of bioactive enediyne mimics such as 1 has required large quantities of acyclic enediyne derivatives 2. For this purpose, we initiated the research for the convenient and practical synthesis of 2 by simple elimination of tert-hydroxy group. Following to this method, we prepared the model 11, which generated the toluene biradical 16 via the eneyne-allene intermediate 15 by means of intramolecular triggering action of hydroxy group under acidic conditions. Compound 11 was found to cleave DNA in acidic conditions. The carboxylic acid 19 which was obtained by the oxidation of 11 was found more reactive than 11. As the other model, we prepared the α-alkynylmalonate 26 following to Nagao's concept. This ester was found to produce the aldehyde 27 by the hydrolysis of ester groups. The mechanism of this reaction was supposed to be the decarboxylation to form the eneyne-allene intermediate, and following Myers-type cyclization, producing the biradical.
- 天然有機化合物討論会の論文
- 1995-09-01
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