多環状多プレニルアシルフロログルシノール類の全合成

抄録

This review focuses on total syntheses of garsubellin A, nemorosone and clusianone, which are polycyclic polyprenylated acylphloroglucinols (PPAPs). The PPAPs feature a highly oxygenated and densely substituted bicyclo[3.3.1]nonane core with prenyl, geranyl, and acyl side chains, and exhibit a wide range of biological activity, including cytotoxicity, antibacterial activity, HIV inhibitory activity, and antioxidant activity etc. These compounds have attracted the considerable attention of organic chemists due to fascinating chemical structures and intriguing biological activities. For total synthesis of this class compounds, several strategies were established and employed to construct a bicyclo[3.3.1]nonane core. Shibasaki-Kanai utilized stereoselective intermolecular aldol reaction, Claisen rearrangement and ring-closing metathesis. Danishefsky employed dearomative allylation, iodocarbocyclization, and bridgehead functionalization reactions. Simpkins and Marazano-Delpech used a Claisen-Deieckmann reaction with malonyl chloride. Porco group employed a double Michael reaction approach.