Bellavance Gabriel, Barriault Louis
Centre for Catalysis, Research and Innovation, Department of Chemistry and Biomolecular Sciences , University of Ottawa , Ottawa K1N 6N5 , Canada.
J Org Chem. 2018 Jul 6;83(13):7215-7230. doi: 10.1021/acs.joc.8b00426. Epub 2018 May 15.
The remarkable biological activities of polyprenylated polycyclic acylphloroglucinols (PPAPs) combined with their highly oxygenated and densely functionalized frameworks have stimulated the interest of synthetic organic chemists over the past decade. Herein, we report the concise total syntheses of four natural products PPAPs, of which some have antibacterial properties, notably hyperforin and papuaforin A. The salient features of this strategy are the short and gram-scalable synthesis of densely substituted PPAPs scaffolds via a Au(I)-catalyzed carbocyclization and the late-stage functionalization for a unified access to a wide variety of PPAPs.
多异戊烯基多环酰基间苯三酚（PPAPs）具有显著的生物活性，再加上其高度氧化和密集官能化的骨架结构，在过去十年中激发了有机合成化学家的兴趣。在此，我们报告了四种天然产物PPAPs的简洁全合成，其中一些具有抗菌特性，特别是贯叶连翘素和巴布亚连翘素A。该策略的显著特点是通过金（I）催化的碳环化反应，以简短且可克级规模合成密集取代的PPAPs支架，并通过后期官能化实现对多种PPAPs的统一合成。
