Formation of 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones via ring-expansion of 4-ethynyl-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones. Total synthesis of methyl linderone |
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| Authors: | Hong Yin Shubhada W DantaleNovruz G Akhmedov Björn CG Söderberg |
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| Institution: | C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045, USA |
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| Abstract: | An in-depth study of the reactions of 4-(ethynyl)-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones with N-bromo- or N-iodosuccinimide, affording in most cases 2-halomethylene-4-cyclopentene-1,3-dione, is described. This reaction was used in a short total synthesis of methyl linderone. |
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| Keywords: | Alkynylcyclobutenones Rearrangement 2-Alkylidene-1 3-cyclopentendiones N-Halosuccinimide Methyl linderone |
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