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Base-assisted intramolecular 6-acetoxypyranone-acetylene [5+2] cycloaddition. Synthesis and reactivity of novel oxa-tricyclo[5.3.1.0]undecenones |
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| Authors: | Sylvain Celanire Frederic Marlin Jack E. Baldwin Robert M. Adlington |
| Affiliation: | Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK |
| Abstract: | The synthesis of 3,11-dioxatricyclo[5.3.1.01,5]undeca-5,9-dien-8-ones is reported from suitable 5-substituted furfuryl alcohols bearing an acetylenic side-chain. Successive peracid-mediated oxidative rearrangement of furan carbinols and base-assisted intramolecular 1,3-dipolar cycloaddition afforded oxygen-bridged tricyclo-undecane derivatives. Stereoselective transformations of cycloadducts are also discussed. |
| Keywords: | Intramolecular [5+2] cycloaddition 3-Oxidopyrilium ylide Acetylenic dipolarophiles Tricyclo[5.3.1.0]undecane Tropolone |
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