Innovation in synthesis strategy is a primary goal of total synthesis. Natural products featuring bornane (camphor-like) skeletal motifs have often been synthesized by routes which construct the key [2.2.1] bicycle at a late stage. Such synthesis strategies tend to arise from classical retrosynthetic paradigms, such as Corey’s strategic bond analysis, which effectively assert that retrosynthetic disconnections which remove the topologically complex bicycle are maximally simplifying. Here, we show that an orthogonal strategy, where the [2.2.1] bicycle is included in a “functionalized camphor” starting material, leads to the shortest known synthesis of the terpenoid longiborneol. Furthermore, we show that selective C–H functionalizations can be used to complete divergent syntheses of a variety of oxidized longiborneol congeners, from a common intermediate.

Total synthesis of longiborneol sesquiterpenoids using a functionalized camphor strategy

ACS Fall 2021

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