Asymmetric Total Synthesis of Cerorubenic Acid-III.
Xin LiuJunyang LiuJianlei WuGuocheng HuangRong LiangLung-Wa ChungChuang-Chuang LiPublished in: Journal of the American Chemical Society (2019)
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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