Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-500 046, India.
Org Biomol Chem. 2022 May 18;20(19):3948-3954. doi: 10.1039/d2ob00438k.
3-Aryllawsones are well known for their wide range of applications in medicinal chemistry, but their synthesis has always remained challenging as no comprehensive protocol has been outlined to date. Owing to their structural importance, we synthesized various 3-aryllawsones with high regioselectivity from simple lawsone and aldehydes in a seven-step double-cascade one-pot reaction through the combination of organocatalytic Ramachary reductive coupling and Hooker oxidation reactions. The commercial availability of the starting materials, diverse substrate scope, possibility of a one- or two-pot approach, regioselectivity of alkyl transfer (with mechanistic proof provided X-ray crystal structure analysis), and numerous medicinal applications of 3-aryllawsones are the key attractions of this work.
3-芳基劳森酮以其在药物化学中的广泛应用而闻名，但由于至今尚无全面的合成方案，其合成一直具有挑战性。鉴于其结构的重要性，我们通过组合有机催化的 Ramachary 还原偶联和 Hooker 氧化反应，从简单的劳森酮和醛出发，在七步双重级联一锅反应中以高区域选择性合成了各种 3-芳基劳森酮。该工作的主要吸引力在于起始原料的商业可得性、底物范围的多样性、一锅或两锅法的可能性、烷基转移的区域选择性（通过 X 射线晶体结构分析提供了机理证明）以及 3-芳基劳森酮的众多医药应用。
