A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products.

ABSTRACT: 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

SUBMITTER: Alfonzo E 

PROVIDER: S-EPMC6761868 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature