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

ABSTRACT: 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 lig

SUBMITTER: Xiang JC 

PROVIDER: S-EPMC9203495 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature