Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration


  • Financial support from GlaxoSmithKline, Pfizer, and the EPSRC is gratefully acknowledged. Dr. Mark Bunnage (Pfizer) is thanked for helpful discussions.


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A transannular ring contraction induced by the addition of an aryl radical intermediate to a proximal arene facilitated the construction of the highly strained macrocyclic core of cavicularin (1). The precursor, an iodinated derivative of another natural product, riccardin C, was prepared from four commercially available arenes in a highly convergent sequence.