1. Universidade Federal do Rio Grande do Norte
2. Instituto de Química
3. IQ - Artigos publicados em periódicos

Título:	Synthesis, NMR data and theoretical study of semi-synthetic derivatives from trans-dehydrocrotonin
Autor(es):	Soares, Breno Almeida Maciel, Maria Aparecida Medeiros Castro, Rosane Nora Kaiser, Carlos R. Firme, Caio Lima
Palavras-chave:	t-DCTN;t-CTN;t-CTN-OL;NMR;QTAIM;DFT
Data do documento:	19-Dez-2015
Editor:	Journal of Molecular Structure
Referência:	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: https://www.sciencedirect.com/science/article/abs/pii/S0022286015305330. Acesso em: 08 jun. 2020.
Resumo:	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
URI:	https://repositorio.ufrn.br/handle/123456789/31554
Aparece nas coleções:	IQ - Artigos publicados em periódicos

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