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Issue 10, 2019
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Synergistic use of NMR computation and quantitative interproton distance analysis in the structural determination of neokadcoccitane A, a rearranged triterpenoid featuring an aromatic ring D from Kadsura coccinea

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Abstract

Neokadcoccitane A (1), an unprecedented 14(13 → 12):28(14 → 8)-diabeo-3,4-secolanostane triterpenoid possessing an aromatic ring D and an unusual Me-21 orientation, along with two novel 14(13 → 12)-abeo-3,4-seco-norlanostane triterpenoids featuring three- and one-carbon degradation, respectively (2 and 3), were isolated from the roots of Kadsura coccinea. The absolute configuration of 1 was determined by the synergistic use of NMR computation, quantitative interproton distance analysis, and TDDFT ECD calculation, while that of 2 was established using X-ray diffraction. 1 was found to exhibit moderate anti-platelet aggregation activity.

Graphical abstract: Synergistic use of NMR computation and quantitative interproton distance analysis in the structural determination of neokadcoccitane A, a rearranged triterpenoid featuring an aromatic ring D from Kadsura coccinea

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Publication details

The article was received on 22 Feb 2019, accepted on 28 Mar 2019 and first published on 29 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00281B
Org. Chem. Front., 2019,6, 1619-1626

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    Synergistic use of NMR computation and quantitative interproton distance analysis in the structural determination of neokadcoccitane A, a rearranged triterpenoid featuring an aromatic ring D from Kadsura coccinea

    H. Xu, K. Hu, X. Shi, J. Tang, X. Li, H. Sun and P. Puno, Org. Chem. Front., 2019, 6, 1619
    DOI: 10.1039/C9QO00281B

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