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Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: total synthesis of egonol

✍ Scribed by Jianwei Zhang; Yi Zhang; Yanshi Zhang; James W Herndon


Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
265 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis


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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