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- W4322489872 abstract "Peribysins belong to a family of eremophilanes isolated from marine Periconia byssoides OUPS-N133 and terrestrial P. macrospinosa KT3863. Their absolute configurations were determined to be the (4S)-enantiomers based on the modified Mosher’s method, chemical derivatizations, density functional theory (DFT)-based electronic circular dichroism (ECD) spectral analysis, and DFT-based [α]D calculations. Danishefsky’s and Reddy’s total syntheses assigned the (4R)-forms for the marine peribysins despite agreeing with the (4S)-configuration for the terrestrial peribysin Q (5). This paper reports the successful solution of this chirality confusion of peribysins by reproducing the ECD spectrum of peribysin G bis(p-bromobenzoate) prepared from peribysin A (1) isolated from terrestrial P. byssoides TS60. 2β-Hydroxyperibysin A (6), which was isolated by changing the culture conditions of the above fungus, was converted to (4S)-peribysin E MTPA esters. These compounds showed identical 1H NMR spectral properties to those reported in the isolation paper. The absolute configurations of peribysins had been determined to be the (4S)-enantiomers in the isolation papers. However, these were revised several times. We isolated peribysin A and 2β-hydroxyperibysin A, which were converted to peribysins G and E, respectively. The chemical correlations, ECD and [α]D analyses successfully resolved the chirality confusion of peribysins." @default.
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- W4322489872 date "2023-04-15" @default.
- W4322489872 modified "2023-09-29" @default.
- W4322489872 title "Termination of the Chirality Confusion of Peribysins" @default.
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- W4322489872 doi "https://doi.org/10.1246/bcsj.20230025" @default.
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