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A Concise Total Synthesis of (±)-Vibralactone
preprintrevised on 24.10.2018, 16:21 and posted on 24.10.2018, 16:25 by Sepand Nistanaki, Luke A. Boralsky, Roy D. Pan, Hosea Nelson
Disclosed is a four-step synthesis of (±)-vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3-prenyl-pyran-2-one forges both the all-carbon quaternary stereocenter and the β-lactone at an early stage. Cyclopropanation of the resulting bicyclic β-lactone furnishes a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. Our concise and modular route to the natural product provides the shortest total synthesis of (±)-vibralactone reported to date.
Read the published paper
in Angewandte Chemie