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Semisynthesis of (-)-Bufospirostenin A Enabled by Photosantonin Rearrangement Reaction.

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An enantioselective semisynthesis of (-)-bufospirostenin A is described. The key steps in the synthesis involve use of our proposed biomimetic and diastereoselective photosantonin rearrangement reaction for construction of the 5/7… Click to show full abstract

An enantioselective semisynthesis of (-)-bufospirostenin A is described. The key steps in the synthesis involve use of our proposed biomimetic and diastereoselective photosantonin rearrangement reaction for construction of the 5/7 bicyclic motif, and a Co-catalyzed reversible double-bond isomerization reaction for installing the double bond in the seven-membered ring.

Keywords: reaction; semisynthesis bufospirostenin; photosantonin rearrangement; rearrangement reaction

Journal Title: Journal of the American Chemical Society
Year Published: 2022

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