The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A

Abstract

Polyprenylated polycyclic acylphloroglucines (PPAPs) are a family of natural products that possess a wide range of different important biological activities because of the relative position and configuration of four substituents that decorate one common central bicyclo[3.3.1]nonane-2,4,9-trione core. The rigid bicyclic framework with its lipophilic side chains and its hydrophilic trione moiety represents a nature-derived lead structure that arranges the substituents (R1 to R4) into a defined topographical orientation. As the substituents are responsible for the biological activities, the seven-step synthetic approach presented here sets the stage for an iterative introduction of R1 to R4 and thus generates structurally diverse trans-type B PPAPs. Four natural and one non-natural trans-type B PPAPs were prepared starting from acetylacetone with overall yields that ranged from 6 to 22%. The concept of separating framework construction from decorating transformations plus the minimization of protecting-group operations are the key issues for the realization of our synthetic approach. The polyprenylated polycyclic acylphloroglucines (PPAPs) are a family of natural products in which a common core is decorated with four different substituents. Here, a synthetic strategy is presented that separates the core building steps from the core decorating steps, offering a general solution to the synthesis of these natural products that will allow investigation of their biological activities.

Cite this article

Biber, N., Möws, K. & Plietker, B. The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A. Nature Chem 3, 938–942 (2011). https://doi.org/10.1038/nchem.1170

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