A novel transformation of 1-exo-substituted 2a-aroyl-1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-ones with sulfoxonium ylide to highly strained 2a-(1-arylethenyl)-1,2,2a,7b-tetrahydrocyclobuta[b]benzofurans |
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| Authors: | Navnath Dnyanoba Yadav Masaki Nagahama Takeshi Sawaki Ai Kurume |
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| Institution: | a Department of Functional Molecular Chemistry, 21st COE Program, Kyoto Pharmaceutical University, Misasagi-Nakauchi 5, Yamashina, Kyoto 607-8414, Japan
b School of Pharmaceutical Sciences, Mukogawa Women’s University, Koshien Kyuban-cho, Nishinomiya 663-8179, Japan |
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| Abstract: | When 1-substituted 2a-aroyl-1,2,2a,8b-tetrahydro-3H-benzob]cyclobutad]pyran-3-ones (1) were treated with dimethylsulfoxonium methylide, 1-endo isomers (endo-1) gave 1-substituted 3-aroyl-1,2,4a,9b-tetrahydrodibenzofuran-4-ols (2) exclusively as expected. On the other hand, 1-exo isomers (exo-1) underwent a novel transformation to 1-substituted 2a-(1-arylethenyl)-1,2,2a,7b-tetrahydrocyclobutab]benzofurans (3), together with 2. |
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| Keywords: | Sulfur ylide 3H-Benzo[b]cyclobuta[d]pyran Cyclobuta[b]benzofuran Tetrahydrodibenzofuran Skelton transformation |
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