Synthesis of a Simple Model Compound of Dynemicin and Cycloaromatization with Pinacol-Pinacolone Rearrangement in the Strained Enediyne Medium Ring

• Toshio Nishikawa

  Laboratory of Organic Chemistry, School of Agriculture, Nagoya University

• Akira Ino

  Laboratory of Organic Chemistry, School of Agriculture, Nagoya University

• Minoru Isobe

  Laboratory of Organic Chemistry, School of Agriculture, Nagoya University

• Toshio Goto

  Laboratory of Organic Chemistry, School of Agriculture, Nagoya University

抄録

Novel bicyclo[7.3.1]-tridecadiyne system included in dynemicin was synthesized from a quinoline aldehyde in 9 steps. Key step was the cyclization with silyl acetylene to ketone carbonyl group through fluoride activation with CsF. The cyclized compound did aromatize under acidic condition, with opening of the epoxide ring, to give a Bergman product that was further converted with pinacol-pinacolone rearrangement.

収録刊行物

• Chemistry Letters

  Chemistry Letters 20 (7), 1271-1274, 1991-07-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360283694085124096
• NII論文ID: 130004418388
• DOI: 10.1246/cl.1991.1271
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/20/7/1271/56062357/cl.1991.1271.pdf
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