Convenient route to centro-substituted triquinacene skeletons via the interrupted Nazarov reaction |
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| Authors: | Ashantai Yungai |
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| Affiliation: | a Department of Chemistry, University of Utah, 315 S. 1400 East, Rm. 2020, Salt Lake City, UT 84112-0850, USA
b Department of Chemistry, University of Alberta, W5-67 Gunning-Lemieux Chemistry Centre, Edmonton, Canada AB T6G 2G2 |
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| Abstract: | Readily available [4 + 3]-cycloadducts derived from trapping of the Nazarov 2-oxidocyclopentenyl cation with 2,3-dimethyl-1,3-butadiene are cleaved by ozonolysis to furnish triketones. In the presence of methanolic KOH, these triones undergo tandem aldol additions to furnish centro-hydroxylated triquinacene skeletons. |
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| Keywords: | Nazarov 4 + 3-Cycloaddition Ozonolysis Aldol Triquinacene |
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