Video Experimental Relacionado

Updated: Mar 13, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Síntesis total de Swinholide A: una exposición en la formación de enlaces C-C mediada por hidrógeno

Inji Shin¹, Suckchang Hong¹, Michael J Krische¹

¹University of Texas at Austin, Department of Chemistry, Austin, TX 78712, USA.

Journal of the American Chemical Society

|November 3, 2016

Resumen

Los investigadores desarrollaron nuevos acoplamientos carbono-carbono mediados por hidrógeno para sintetizar el swindle A de manera eficiente. Este avance reduce significativamente los pasos sintéticos, ofreciendo un enfoque más simplificado para la construcción de moléculas complejas.

Área de la Ciencia:

Química orgánica
Química sintética
Productos naturales del mar

Sus antecedentes:

Swinholide A es un complejo policetídeo marino con actividad biológica significativa, incluida la unión a la actina.
Las anteriores síntesis totales de swinholide A eran largas y complejas, lo que limitaba la accesibilidad.
El desarrollo de metodologías sintéticas eficientes es crucial para la síntesis de productos naturales.

Objetivo del estudio:

Desarrollar una síntesis total muy eficiente y concisa de swinholide A.
Introducir y mostrar nuevas reacciones de acoplamiento carbono-carbono mediadas por hidrógeno.
Demostrar una mejora significativa en la eficiencia sintética en comparación con las rutas anteriores.

Principales métodos:

Utilizó diversas reacciones de acoplamiento carbono-carbono mediadas por hidrógeno.
Empleado una estrategia redox-económica.
Logró altos niveles de quimioterapia y estereoselectividad.

Principales resultados:

Con éxito sintetizó el swindle A en sólo 15 pasos lineales.
Se redujo el número de pasos sintéticos en aproximadamente un 50% en comparación con las síntesis anteriores.
Demostró la utilidad de los acoplamientos mediados por hidrógeno en la síntesis de moléculas complejas.

Conclusiones:

La vía sintética desarrollada representa un avance sustancial en la síntesis total de swindle A.
Los acoplamientos C-C mediados por hidrógeno ofrecen una nueva herramienta poderosa y eficiente para la síntesis orgánica.
Esta metodología proporciona una vía más accesible a swholide A y potencialmente a otras policetidas complejas.

Más Videos Relacionados

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Videos de Conceptos Relacionados

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Formation of Halohydrin from Alkenes

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...