Natural Product Synthesis & Chemical Biology

16. Scalable Total Synthesis of rac-Jungermannenones B and C

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Reported is the first scalable synthesis of rac‐jungermannenones B and C starting from the commercially available and inexpensive geraniol in 10 and 9 steps, respectively. The unique jungermannenone framework is rapidly assembled by an unprecedented regioselective 1,6‐dienyne reductive cyclization reaction which proceeds through a vinyl radical cyclization/allylic radical isomerization mechanism. DFT calculations explain the high regioselectivity observed in the 1,6‐dienyne reductive radical cyclization.

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