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Issue 33, 2019
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A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

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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 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.

Graphical abstract: A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

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Publication details

The article was received on 02 Jun 2019, accepted on 30 Jun 2019 and first published on 05 Jul 2019


Article type: Edge Article
DOI: 10.1039/C9SC02682G
Chem. Sci., 2019,10, 7746-7754
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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

    E. Alfonzo and A. B. Beeler, Chem. Sci., 2019, 10, 7746
    DOI: 10.1039/C9SC02682G

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      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
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      [Original citation] - Published by The Royal Society of Chemistry.

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