1H and13C NMR signal assignments of a novel Baeyer-Villiger originated diterpene lactone

Vieira, Henriete S.; Takahashi, Jacqueline A.; Gunatilaka, A. A. Leslie; Boaventura, Maria Amélia D.

doi:10.1002/mrc.1738

Cited by 3 publications

(2 citation statements)

References 13 publications

(25 reference statements)

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“…However, to date, only 1 H-NMR chemical shifts assignments of 4 have been published. The 2D NMR (HSQC, HMBC, COSY and NOESY) data are essential to elucidate the stereochemistry of PCTTs due to their complex structures [9,10]. The analysis of 2D NMR spectral data contributed to establish the correct chemical shift assignments of all carbons and hydrogens of compound 4.…”

Section: Introductionmentioning

confidence: 99%

The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems

2016

Spectroscopy

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Friedelin (1), 3β-friedelinol (2), 28-hydroxyfriedelin (3), 16α-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16α,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl 3 solution, 16α-hydroxyfriedelin (4) reacted turning into 3-oxo-16-methylfriedel-16-ene (7). This is the first report of a dehydration followed by a Nametkin rearrangement of a pentacyclic triterpene in CDCl 3 solution occurring in the NMR tube. These seven pentacyclic triterpenes was identified through NMR spectroscopy and the stereochemistry of compound 4 and 7 was established by 2D NMR (NOESY) spectroscopy and mass spectrometry (GC-MS). It is also the first time that all the 13 C-NMR and 2DNMR spectral data are reported for compounds 4 and 7.

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Section: Introductionmentioning

confidence: 99%

The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems

2016

Spectroscopy

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“…However, to date, only 1 H-NMR chemical shifts assignments of 4 have been published. The 2D NMR (HSQC, HMBC, COSY and NOESY) data are essential to elucidate the stereochemistry of PCTTs due to their complex structures [ 9 , 10 ]. The analysis of 2D NMR spectral data contributed to establish the correct chemical shift assignments of all carbons and hydrogens of compound 4 .…”

Section: Introductionmentioning

confidence: 99%

Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy

et al. 2009

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Friedelin (1), 3β-friedelinol (2), 28-hydroxyfriedelin (3), 16α-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16α,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl3 solution, 16α-hydroxyfriedelin (4) reacted turning into 3-oxo-16-methylfriedel-16-ene (7). This is the first report of a dehydration followed by a Nametkin rearrangement of a pentacyclic triterpene in CDCl3 solution occurring in the NMR tube. These seven pentacyclic triterpenes was identified through NMR spectroscopy and the stereochemistry of compound 4 and 7 was established by 2D NMR (NOESY) spectroscopy and mass spectrometry (GC-MS). It is also the first time that all the 13C-NMR and 2D NMR spectral data are reported for compounds 4 and 7.

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Montanoa tomentosa glandular trichomes containing kaurenoic acids chemical profile and distribution

Robles‐Zepeda¹,

Lozoya‐Gloria²,

López³

et al. 2009

Fitoterapia

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1H and13C NMR signal assignments of a novel Baeyer-Villiger originated diterpene lactone

Cited by 3 publications

References 13 publications

The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems

The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems

Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy

Montanoa tomentosa glandular trichomes containing kaurenoic acids chemical profile and distribution

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