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Novel stereoconvergent transformation of 1,2a-disubstituted 1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-ones to 1,3-disubstituted 1,2,4a,9b-tetrahydrodibenzofuran-4-ols and its application to the second-generation synthesis of (±)-linderol A

✍ Scribed by Yamashita, Masayuki; Inaba, Tomoki; Nagahama, Masaki; Shimizu, Takashi; Kosaka, Sachiko; Kawasaki, Ikuo; Ohta, Shunsaku

Book ID
119963410
Publisher
Royal Society of Chemistry
Year
2005
Tongue
English
Weight
326 KB
Volume
3
Category
Article
ISSN
1477-0520

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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
✍ Navnath Dnyanoba Yadav; Masayuki Yamashita; Masaki Nagahama; Tomoki Inaba; Takes 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 128 KB

When 1-substituted 2a-aroyl-1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta [d]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) u