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Rapid construction of polycyclic ring systems from aromatics: stereoselective synthesis of the carbon framework of vinigrol |
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| Authors: | Yan-Bin Lu Day-Shin Hsu Chun-Chen Liao |
| Institution: | 1. Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan;2. Department of Chemistry and Biochemistry, National Chung Cheng University, Minhsiung 621, Taiwan;3. Department of Chemistry, Chung Yuan Christian University, Chungli 320, Taiwan |
| Abstract: | The stereoselective syntheses of the tricyclic core structure of vinigrol and highly functionalized polycyclic molecules from 5-bromo-2-methoxyphenol in five synthetic steps are reported. Intramolecular and intermolecular Diels–Alder reactions and tandem oxy-Cope/ene reactions are the key steps in the synthesis. |
| Keywords: | Masked o-benzoquinones Oxy-Cope rearrangement Ene reaction Tandem reaction Polycycles |
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