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Asymmetric Total Synthesis of the Highly Strained 4β-Acetoxyprobotryane-9β,15α-diol

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https://figshare.com/articles/dataset/Asymmetric_Total_Synthesis_of_the_Highly_Strained_4_-Acetoxyprobotryane-9_15_-diol/13221773
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The first and asymmetric total synthesis of 4β-acetoxyprobotryane-9β,15α-diol, containing a rare and highly strained trans-fused bicyclo­[3.3.0]­octane ring system, has been achieved. The synthetically challenging [6–5–5] tricyclic ring system in the final product was efficiently and diastereoselectively synthesized via an asymmetric rhodium-catalyzed [4 + 2] cycloaddition reaction, followed by a unique benzilic acid type rearrangement under very mild conditions. The seven contiguous stereocenters were installed efficiently and diastereoselectively.
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2020-11-11
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