139501-40-9Relevant articles and documents
A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products
Alfonzo, Edwin,Beeler, Aaron B.
, p. 7746 - 7754 (2019/08/30)
Herein, we detail a unified synthetic approach to the classical lignan family of natural products that hinges on divergence from a common intermediate that was strategically identified from nature's biosynthetic blueprints. Efforts toward accessing the common intermediate through a convergent and modular approach resulted in the discovery of a sterically encumbered photoredox catalyst that can selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2-4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural functionality was demonstrated, which establishes the potential of this strategy to accelerate structure-activity-relationship studies of these natural product frameworks and their rich biological activity.
Synthesis, anti-virus and anti-tumour activities of dibenzylbutyrolactone lignans and their analogues
Xia, Yamu,You, Jia,Zhang, Yuanyuan,Su, Zhongliang
experimental part, p. 565 - 569 (2010/03/03)
An efficient synthesis of dibenzylbutyrolactone lignans and their analogues has been developed. Based on a Stobbe condensation of piperonal or veratraldehyde with diethylsuccinate and alkylation with 3,4- methylenedioxybenzyl bromide to give the skeleton
Asymmetric Syntheses of Lignans of the Dibenzylbutyrolactone, Dibenzylbutanediol, Aryltetralin and Dibenzocyclooctadiene Series
Pelter, Andrew,Ward, Robert S.,Jones, D. Martin,Maddocks, Peter
, p. 239 - 242 (2007/10/02)
General procedures are outlined for the asymmetric syntheses of ligands of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetralin and dibenzocyclooctadiene series, from tandem addition products derived from 4-mentyloxybutenolide.