An electrochemical ODI‐[5+2] cascade reaction was developed which enables the rapid assembly of diversely functionalized bicyclo[3.2.1]octadienones from sensitive ethynylphenols. By combining a directed retro‐aldol/aldol process, a [2,3]‐sigmatropic rearrangement, and an Al(O‐iPr)3‐promoted reductive 1,3 ‐transposition, the asymmetric total syntheses of five 8,9‐seco‐ent‐kauranoids—(−)‐shikoccin, (−)‐O‐methylshikoccin, (−)‐epoxyshikoccin, (+)‐O‐methylepoxyshikoccin, and (+)‐rabdo‐hakusin—have been achieved in a concise and efficient manner.
An electrochemical ODI‐[5+2] cascade reaction was developed which enables the rapid assembly of diversely functionalized bicyclo[3.2.1]octadienones from sensitive ethynylphenols. By combining a directed retro‐aldol/aldol process, a [2,3]‐sigmatropic rearrangement, and an Al(O‐iPr)3‐promoted reductive 1,3‐transposition, the asymmetric total syntheses of five 8,9‐seco‐ent‐kauranoids—(−)‐shikoccin, (−)‐O‐methylshikoccin, (−)‐epoxyshikoccin, (+)‐O‐methylepoxyshikoccin, and (+)‐rabdo‐hakusin—have been achieved in a concise and efficient manner.
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