Total Synthesis of Aplydactone by a Conformationally Controlled C−H Functionalization

Angewchem
Total Synthesis of Aplydactone by a Conformationally Controlled C−H Functionalization: A concise, protecting‐group‐free total synthesis of the unusual brominated sesquiterpene aplydactone is described. Our synthesis features a [2+2] photocycloaddition, a Wolff ring contraction, an unusual remote C−H functionalization to establish the highly strained tetracyclic core, and a hydrogen-atom transfer (HAT) reaction to access the bromine-containing stereocenter.

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