Assignment of 1H and 13C spectra and investigation of hindered side‐chain rotation in lupeol derivatives †
@article{Burns2000AssignmentO1, title={Assignment of 1H and 13C spectra and investigation of hindered side‐chain rotation in lupeol derivatives †}, author={D. C. Burns and W. Reynolds and Greg O. Buchanan and P. Reese and R. Enr{\'i}quez}, journal={Magnetic Resonance in Chemistry}, year={2000}, volume={38} }
Complete 1H and 13C spectral assignments are reported for lupeol (1a) and two derivatives where the C‐30 methyl group is replaced by CH2OH (1b) and HC O (1c). Compound 1c shows conformationally dependent substituent effects on 1H chemical shifts. It also shows line broadening of some 13C signals at 25 °C, suggesting hindered rotation of the side‐chain group. This is confirmed by low‐temperature spectra which show splitting of broadened peaks into pairs in a ca 2 : 1 area ratio. The free energy… CONTINUE READING
83 Citations
Identification and complete 1H and 13C spectral assignments for the triterpene fern‐9(11)‐en‐28‐oic acid
- Chemistry
- 2001
- 4
Structural and 1H and 13C NMR analysis of two new glabretal triterpenoid derivatives from Guarea jamaicensis
- Chemistry
- 2001
- 4
1H and 13C assignments of two new triterpenes from Cladocolea grahami
- Chemistry, Medicine
- Magnetic resonance in chemistry : MRC
- 2004
- 5
Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.
- Chemistry, Medicine
- Journal of natural products
- 2012
- 30
Structure elucidation and NMR assignments of two new triterpenoids from the stems of Paragonia pyramidata (Bignoniaceae)
- Chemistry, Medicine
- Magnetic resonance in chemistry : MRC
- 2011
- 6
Salicassin, an Unprecedented Chalcone ? Diterpene Adduct and a Quinone Methide Triterpenoid from Maytenus salicifolia
- Chemistry
- 2013
- 3
Oxidation at C-16 enhances butyrylcholinesterase inhibition in lupane triterpenoids.
- Chemistry, Medicine
- Bioorganic chemistry
- 2018
- 3
- PDF
Rational design and synthesis of topoisomerase I and II inhibitors based on oleanolic acid moiety for new anti-cancer drugs.
- Chemistry, Medicine
- Bioorganic & medicinal chemistry
- 2014
- 18
References
SHOWING 1-10 OF 11 REFERENCES
Proton chemical shifts in NMR. Part 13.1 Proton chemical shifts in ketones and the magnetic anisotropy and electric field effect of the carbonyl group
- Chemistry
- 1999
- 29
- PDF
Steric effects on carbon‐13 NMR shifts: carbon–hydrogen bond polarization contributions
- Chemistry
- 1998
- 27
The Investigation of the Kinetics of Conformational Changes by Nuclear Magnetic Resonance Spectroscopy
- Chemistry
- 1972
- 125
Six new triterpenoids and other triterpenoids and steroids from three Quercus species of Hong Kong.
- Chemistry, Medicine
- Journal of the Chemical Society. Perkin transactions 1
- 1977
- 20