Rearrangement approaches to cyclic skeletons. III. Practical route to cis-bicyclo(4.3.0)non-4-en-7-ones based on photochemical (1,3) acyl migration of bicyclo(3.2.2)non-6-en-2-ones.

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概要

• 論文の詳細を見る

• 1-Methoxybicyclo[3.2.2]non-6-en-2-ones and the related compounds were derived I) from the Diels-Alder type 1,4-addition products of tropones with ethylene by selective reduction of the α,β-unsaturated carbonyl part (hydrosilylation followed by hydrolysis) and/or II) from bicyclo[2.2.2]oct-5-en-2-ones a) by the ring-enlargement utilizing Tieffeneau-Demjanov type conditions (1, TMS–CN; 2, LiAlH<SUB>4</SUB>; 3, NaNO<SUB>2</SUB>–AcOH) and/or b) by the related ringexpansion using trimethylsilyldiazomethane and boron trifluoride etherate. These bridged compounds were transformed into the respective [1,3] acyl migration products, <I>cis</I>-bicyclo[4.3.0]non-4-en-7-ones, in practical yields by direct irradiation through a Pyrex filter.

• 公益社団法人 日本化学会の論文

著者

• Uyehara Tadao

  Department Of Applied Chemistry Faculty Of Engineering Utsunomiya University

• Furuta Toshiaki

  Department Of Biomolecular Science Faculty Of Sciece Toho University

• Kabasawa Yasuhiro

  Department Of Sport And Medical Science Faculty Of Physical Education Kokushikan University

• Kato Tadahiro

  Department of Applied Microbial Technology, Kumamoto Institute of Technology

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