Journal
ORGANIC LETTERS
Volume 18, Issue 18, Pages 4730-4733Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02404
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Funding
- National Natural Science Foundation of China [21502093, 21302096]
- Natural Science Foundation of Jiangsu Province [BK20150871, BK20130962]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
- Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions (TAPP)
- Australian Research Council [DP160101682]
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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.
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