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The University of Southampton

Research project: Harrowven: Total Synthesis of Cavicularin and Riccardin C

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Cavicularin, from the liverwort Cavicularia densa, is one of the most unusual and synthetically challenging natural products to have been isolated in the last decade. Comprised of a macrocyclic core containing dibenzyl and dihydrophenanthrene units conjoined by a biaryl bond and an ether linkage, this imparts such strain on the system that arene A is forced to adopt a boat like configuration, being twisted out of the plane by some 15° in the solid state (see Figure).

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We secured the first total synthesis of cavicularin using a radical induced transannular ring contraction to construct the strained macrocyclic core.

We have recently completed a short, second generation synthesis of riccardin C and are working towards the first asymmetric total synthesis of (+)-cavicularin.



Related research groups

Organic Chemistry: Synthesis, Catalysis and Flow
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