Isolation of the 3′R and 3′S diastereomers of fasciculic acid C from the Australian mushroom Hypholoma australianum
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Ward, BT
Elnaas, AR
Zunk, M
Holland, DC
May, TW
Voser, TM
Abitbol, A
Cooper, O
Tiralongo, J
Grice, ID
Carroll, AR
Tiralongo, E
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Abstract
Nine compounds including the new diastereomers (3′R)-fasciculic acid C (1) and (3′S)-fasciculic acid C (2), the triterpenes (3–5), the sesquiterpenes (6–7) and the diketopiperazines (8–9) were isolated from the Australian mushroom Hypholoma australianum. Several lanostane triterpenes have been isolated from the genus Hypholoma previously contain a 3-hydroxy-3-methylglutaric acid or a 3-hydroxy-3-methylglutaryl-glycine side chain. Only Hypholoma derived triterpenes possessing the S-configuration for these two side chains have been isolated previously. Compound 1 is the first example of a triterpene isolated from Hypholoma to have an R-configuration for the side chain.
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Tetrahedron Letters
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78
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Medicinal and biomolecular chemistry
Medicinal and biomolecular chemistry not elsewhere classified
Macromolecular and materials chemistry
Organic chemistry
Biochemistry and cell biology
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Hayton, JB; Ward, BT; Elnaas, AR; Zunk, M; Holland, DC; May, TW; Voser, TM; Abitbol, A; Cooper, O; Tiralongo, J; Grice, ID; Carroll, AR; Tiralongo, E, Isolation of the 3′R and 3′S diastereomers of fasciculic acid C from the Australian mushroom Hypholoma australianum, Tetrahedron Letters, 2021, 78, pp. 153294