Determinación de la estereoquímica de telepamida y enigmazol C mediante cálculos computacionales, reacciones de cicloisomerización de 1, 5-eninos catalizadas por indio (III), y síntesis total de ircinialactama J

Resumo

This PhD Thesis presents the research work based on the use of computational methods for structural determination of organic compounds, the use of synthetic methodology by catalysis and the total synthesis of a marine natural product. In chapter I, the stereochemistry of natural products thelepamide and enigmazole C is studied by computational calculations using DFT methods; the stereochemistry of thelepamide is revised and its absolute configuration is confirmed. The absolute configuration of enigmazole C is also determined using computational methods and configurational analysis based on coupling constants (JBCA). Chapter II studies the catalytic activity of halides and salts of indium(III) in cycloisomerization reactions of functionalized aryl 1,5-enynes. The double cyclization reaction takes place in a cascade way with 6-endo-dig regioselectivity, achieving the formation of new carbon-carbon and carbon-oxygen bonds, allowing access to new polycyclic structures. Chapter III describes the first total synthesis of ircinialactam J, a natural product isolated from the sponge Ircinia felix, with remarkable antiviral activity. The synthesis, based on a convergent strategy, also enables to confirm the proposed structure and allows access to interesting derivatives.