Accessing complex, bioactive natural products remains a challenge for synthetic chemists; however, employing strategic reaction sequences allows for the synthesis of such structures. One natural product, cochlearol B, presents unique synthetic challenges as the core of this pentacyclic compound is composed of a bicyclo[3.2.0]heptane whose cyclobutane contains three stereocenters. A sequence initiated with a Kabbe condensation to access this scaffold was utilized to synthesize enantiopure cochlearol B. By building onto the formed chromenone with a Catellani reaction, an intermediate capable of undergoing a visible-light-mediated photocycloaddition to yield the core of this renoprotective meroterpenoid was established. Ensuing functionalization to form the α,β-unsaturated aldehyde moiety completes the synthesis of cochlearol B in a 12-step sequence.

Total synthesis of cochlearol B

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