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