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Asymmetric Total Synthesis of Cerorubenic Acid-III
Xin Liu1,2, Junyang Liu1,3, Jianlei Wu1
1Shenzhen Grubbs Institute, Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.
Abstract:
The first asymmetric total synthesis of the highly strained compound cerorubenic acid-III is reported. A type II intramolecular [5 + 2] cycloaddition allowed efficient and diastereoselective construction of the synthetically challenging bicyclo[4.4.1] ring system with a strained bridgehead (anti-Bredt) double bond in the final product. A unique transannular cyclization installed the vinylcyclopropane moiety with retention of the desired stereochemistry.
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