23343-24-0Relevant articles and documents
Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: Total synthesis of egonol
Zhang, Jianwei,Zhang, Yi,Zhang, Yanshi,Herndon, James W.
, p. 5609 - 5616 (2003)
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.