Gold-Catalyzed Tandem 1,3-Migration/Double Cyclopropanation of 1-Ene-4,n-diyne Esters to Tetracyclodecene and Tetracycloundecene Derivatives

Cuili Chen, Yongzhen Zou, Xianxiao Chen, Xiaoxiang Zhang, Weidong Rao, Philip Wai Hong Chan

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A synthetic method that relies on Au(I)-catalyzed tandem 1,3-acyloxy migration/double cyclopropanation of 1-ene-4,9-diyne and 1-ene-4,10-diyne esters to construct the respective architecturally challenging tetracyclodecene and tetracycloundecene derivatives is described. Achieved under mild reaction conditions, the transformation was shown to be robust with a wide variety of substitution patterns tolerated to give the two members of the carbocyclic family in good to excellent yields and as a single regio- and diastereomer.

Original languageEnglish
Pages (from-to)4730-4733
Number of pages4
JournalOrganic Letters
Issue number18
Publication statusPublished - 16 Sep 2016

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