Total Synthesis of (−)-Zearalenone and (−)-Zearalanone: A Macrocyclization Strategy by Ni/Zr/Cr-Mediated Reductive Ketone Coupling

The total synthesis of the resorcylic acid lactones (-)-zearalenone and (-)-zearalanone is described. Our synthetic strategy relies on Ni-, Zr-, and Cr-mediated intramolecular reductive ketone coupling to create 14-membered macrolactones. Notably, the use of CrCl<sub>2</sub> in addition to Ni/Zr-mediated reductive ketone coupling conditions was key for the success of the macrocyclization.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-10
DOI
https://doi.org/10.1021/acs.joc.4c01793
Citations
5
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
1.25

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article

Total Synthesis of (−)-Zearalenone and (−)-Zearalanone: A Macrocyclization Strategy by Ni/Zr/Cr-Mediated Reductive Ketone Coupling

Atsushi Umehara, Makoto Sasaki, K. Kawakita
5 citations
The Journal of Organic Chemistry
Synthetic Organic Chemistry Methods
1.25
article

Total Synthesis of (−)-Zearalenone and (−)-Zearalanone: A Macrocyclization Strategy by Ni/Zr/Cr-Mediated Reductive Ketone Coupling

Atsushi Umehara, Makoto Sasaki, K. Kawakita
article en
5 citations

Abstract

The total synthesis of the resorcylic acid lactones (-)-zearalenone and (-)-zearalanone is described. Our synthetic strategy relies on Ni-, Zr-, and Cr-mediated intramolecular reductive ketone coupling to create 14-membered macrolactones. Notably, the use of CrCl<sub>2</sub> in addition to Ni/Zr-mediated reductive ketone coupling conditions was key for the success of the macrocyclization.

The Journal of Organic ChemistryVol. 89(18)
Tohoku University (JP)
Japan Society for the Promotion of Science
Openalex Percentile: Top 23%
Synthetic Organic Chemistry Methods
1.25
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