Taming the radical cation intermediate enabled one-step access to structurally diverse lignans

Lignans, in spite of their structural diversity, are all biosynthetically derived from coniferyl alcohol. We report herein a divergent synthesis of lignans from biomass-derived monolignols in a short synthetic sequence. Blue LED irradiation of a dichloromethane solution of dicinnamyl ether derivatives in the presence of Cu(TFA)2, an alcohol (2.0 equiv) and a catalytic amount of Fukuzumi’s salt affords the C7-alkoxylated aryltetralin cyclic ethers. Increasing the amount of alcohol under otherwise identical conditions diverts the reaction course to furnish the C7,C7’-dialkoxylated dibenzyltetrahydrofurans, while replacing Cu(TFA)2 with diphenyl disulfide (PhSSPh) provides selectively the C7 monoalkoxylated dibenzyltetrahydrofurans. Aza-, thia- and carba-analogues of lignans are equally accessible by simply changing the tethering atom of the allylic alcohols. Concise total syntheses of aglacins A, E, F, brassilignan, and dehydrodimethylconidendrin are documented featuring these transformations.

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Jieping Zhu, Cédric Fung, Qiang Wang, Jia-Chen Xiang
2022
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Abstract

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https://infoscience.epfl.ch/record/294777?ln=en

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Related concepts (5)

Divergent synthesis

In chemistry a divergent synthesis is a strategy with the aim to improve the efficiency of chemical synthesis. It is often an alternative to convergent synthesis or linear synthesis. In one strategy divergent synthesis aims to generate a library of chemical compounds by first reacting a molecule with a set of reactants. The next generation of compounds is generated by further reactions with each compound in generation 1. This methodology quickly diverges to large numbers of new compounds A generates A1, A2, A3, A4, A5 in generation 1 A1 generates A11, A12, A13 in generation 2 and so on.

Accessibility

Accessibility is the design of products, devices, services, vehicles, or environments so as to be usable by people with disabilities. The concept of accessible design and practice of accessible development ensures both "direct access" (i.e. unassisted) and "indirect access" meaning compatibility with a person's assistive technology (for example, computer screen readers). Accessibility can be viewed as the "ability to access" and benefit from some system or entity.

Catalytic converter

A catalytic converter is an exhaust emission control device that converts toxic gases and pollutants in exhaust gas from an internal combustion engine into less-toxic pollutants by catalyzing a redox reaction. Catalytic converters are usually used with internal combustion engines fueled by gasoline or diesel, including lean-burn engines, and sometimes on kerosene heaters and stoves. The first widespread introduction of catalytic converters was in the United States automobile market. To comply with the U.S.