Journal of the American Chemical Society· 2026Q1
Concise Total Syntheses of (−)-Ohioensin A, Putative (+)-Ohioensin C, (+)-Myristinins A and B/C, and (+)-Caesalpinflavan A
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- Q1SCImago
- 2026year
Short summary
A unified synthetic approach delivers the first concise enantioselective total syntheses of (−)-ohioensin A, putative (+)-ohioensin C, and related flavonoids (+)-myristinins A and B/C, and (+)-caesalpinflavan A.
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Key points
- First concise enantioselective total syntheses of (−)-ohioensin A and putative (+)-ohioensin C achieved.
- Flavonoids (+)-myristinins A and B/C, and (+)-caesalpinflavan A also synthesized.
- Key methodologies include chiral biphenol-catalyzed conjugate addition and stereodivergent cyclization.
- Strategy enables access to both cis- and trans-2,4-disubstituted benzodihydropyrans.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract The ohioensins represent a distinct class of polycyclic benzonaphthoxanthenone natural products that share structural similarities with flavonoids. Herein, we disclose a unified synthetic approach that culminates in the first concise enantioselective total syntheses of (−)-ohioensin A and putative (+)-ohioensin C, as well as the flavonoids (+)-myristinins A and B/C and (+)-caesalpinflavan A. The synthetic strategy hinges on the development of novel methodologies, including a chiral biphenol-catalyzed enantioselective conjugate addition of alkenyl and aryl boronic acids to 2-hydroxynitrostyrenes, a stereodivergent cyclization to procure both cis- or trans-2,4-disubstituted benzodihydropyrans, and an intramolecular deaminative aromatic homolytic substitution.
The authors' abstract, as published at the source. Journal of the American Chemical Society, 2026 · DOI ↗
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Field: Biochemistry (Biochemistry, Genetics and Molecular Biology)
BiochemistryBiochemistry, Genetics and Molecular Biology