Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: total synthesis of egonol |
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Authors: | Jianwei ZhangYi Zhang Yanshi ZhangJames W Herndon |
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Affiliation: | Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003, USA |
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Abstract: | The reaction of various carbene complexes with dienylacetylenes has been examined. The reaction has been used as the cornerstone for the preparation of the nor-neolignan natural product egonol in five steps from readily available components. In most examples of the carbene-alkyne coupling, the reaction proceeds to form benzofuran derivatives. In the case of one highly functionalized terminal alkyne, a competing rearrangement/cyclization process occurs in preference to the carbene coupling process. The use of silylated alkynes subverts this process. |
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Keywords: | carbene complexes benzofuran Sonogashira coupling conjugated alkynes |
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