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Title: Synthesis, NMR data and theoretical study of semi-synthetic derivatives from trans-dehydrocrotonin
Authors: Soares, Breno Almeida
Maciel, Maria Aparecida Medeiros
Castro, Rosane Nora
Kaiser, Carlos R.
Firme, Caio Lima
Issue Date: 19-Dec-2015
Publisher: Journal of Molecular Structure
Citation: SOARES, Breno Almeida; MACIEL, Maria Aparecida Medeiros; CASTRO, Rosane Nora; KAISER, Carlos Roland; FIRME, Caio Lima. Synthesis, NMR data and theoretical study of semi-synthetic derivatives from trans- dehydrocrotonin. Journal Of Molecular Structure, [S.l.], v. 1108, p. 533-541, mar. 2016. Disponível em: Acesso em: 08 jun. 2020.
Portuguese Abstract: In this work, the 19-nor-diterpenoid clerodane-type dehydrocrotonin (t-DCTN) was a primary source for a two-step synthetic procedure. The catalytic hydrogenation of t-DCTN afforded the semi-synthetic trans- crotonin (t-CTN) in a highly stereospecific reaction confirmed by DFT calculations. The unsaturated carbonyl group of t-DCTN was reduced by NaBH4/EtOH providing an epimeric a-OH and b-OH mixture named t-CTN-OL. Both epimeric compound structures t-CTN-a-OL and t-CTN-b-OL were elucidated by 1D and 2D NMR spectral data. Comparison of NMR data from natural source of t-CTN was done to confirm the stereochemical authenticity of semi-synthetic t-CTN. Calculated NMR data for all described de- rivatives (semi-synthetic t-CTN and its t-CTN-OL epimeric mixture) were performed using B3LYP/6- 311Gþþ(d,p) level of theory which validated our previously developed NMR theoretical protocol for structural analyses of organic molecules. Topological data using Quantum Theory of Atoms in Molecules (QTAIM) of t-CTN quantified and qualified intramolecular interactions of its most stable conformer
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