First synthesis of both enantiomers of pseudohygrophorone A12, an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola
Pseudohygrophorone A12, a highly oxygenated cyclohexenone derivative isolated from Hygrophorus abieticola, exhibits anti-fungal activity against several phytopathogenic fungi and oomycete. The first synthesis of both enantiomers of pseudohygrophorones A12 was accomplished starting from an optically...
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Veröffentlicht in: | Tetrahedron 2019-09, Vol.75 (38), p.130528, Article 130528 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Pseudohygrophorone A12, a highly oxygenated cyclohexenone derivative isolated from Hygrophorus abieticola, exhibits anti-fungal activity against several phytopathogenic fungi and oomycete. The first synthesis of both enantiomers of pseudohygrophorones A12 was accomplished starting from an optically active sulfoxide. In our approach, the diastereoselective Michael−aldol cascade reaction was featured as the key step.
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•The first synthesis of both enantiomers of pseudohygrophorone A12 was achieved.•Pseudohygrophorone A12 is a highly oxygenated cyclohexenone derivative with anti-fungal activity.•An optically active sulfoxide was used as the chiral starting material.•Michael-aldol cascade reaction was featured as the key step. |
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2019.130528 |