Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

Ujiie, Kazuki; Tanaka, Chiaki; Arai, Masayoshi; Hashimoto, Masaru; Yoshida, Yuki; Kawano, Tomikazu; Tamura, Satoru

doi:10.1007/s11418-024-01810-5

J Nat Med

2024

DOI: 10.1007/s11418-024-01810-5

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Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

Kazuki Ujiie,

Chiaki Tanaka,

Masayoshi Arai

et al.

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Triantaspirols A–C and Paraphaeolactone Cs from Paraphaeosphaeria sp. KT4192: Sensitivity of CP3 in Distinguishing Close NMR Signals

Kanehara,

Oinuma,

Maeda

et al. 2024

J. Nat. Prod.

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Hybridized spirobisnaphthalene derivatives, triantaspirols A−C (1−3) and paraphaeolactones C1 and C2 (4 and 5), were identified from the culture broth of the fungus Paraphaeosphaeria sp. KT4192. The NMR spectra of 2 and 3, as well as 4 and 5, closely resembled each other, indicating that these were pairs of diastereomers. Although this NMR spectral resemblance made it challenging to distinguish their relative configurations, detailed analysis of the electronic circular dichroism (ECD) spectra and NOE correlations allowed us to deduce them. The CP3 metric with the DFT-based NMR chemical shifts was found to distinguish configurations of diastereomers in a highly sensitive and accurate manner that DP4 could not account for because of the very close chemical shift differences in the experimental NMR spectra. The reliability of this method was assessed using 23 published examples which could not be distinguished by DP4 protocol.

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Triantaspirols A–C and Paraphaeolactone Cs from Paraphaeosphaeria sp. KT4192: Sensitivity of CP3 in Distinguishing Close NMR Signals

Kanehara,

Oinuma,

Maeda

et al. 2024

J. Nat. Prod.

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show abstract

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Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

Cited by 1 publication

References 36 publications

Triantaspirols A–C and Paraphaeolactone Cs from Paraphaeosphaeria sp. KT4192: Sensitivity of CP3 in Distinguishing Close NMR Signals

Triantaspirols A–C and Paraphaeolactone Cs from Paraphaeosphaeria sp. KT4192: Sensitivity of CP3 in Distinguishing Close NMR Signals

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