Video Experimental Relacionado

Updated: Jul 19, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Síntesis total de la (+/-) -cartelina C en su conjunto

Phil S Baran¹, Ryan A Shenvi

¹Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.

Journal of the American Chemical Society

|October 26, 2006

Resumen

La primera síntesis total de la chartelina C se logró en 10 pasos. Este avance en la química heterocíclica utilizó nuevos métodos para la instalación de halógenos y la contracción de anillos.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
Química Heterocíclica La Química Heterocíclica es una de las más conocidas.

Sus antecedentes:

Chartelline C es un producto natural complejo con una estructura molecular desafiante.
Los esfuerzos anteriores para sintetizar la chartelina C no han tenido éxito, dejando su síntesis total como un desafío de larga data.

Objetivo del estudio:

Para informar de la primera síntesis total concisa y concisa de (+/-) -chartelline C.
Desarrollar y mostrar nuevas metodologías sintéticas aplicables a compuestos heterocíclicos complejos.

Principales métodos:

Se diseñó y ejecutó una secuencia sintética de 10 pasos.
Los pasos clave incluyeron la halogenación selectiva por quimioterapia y posición, la reducción selectiva de alquinos y una termólisis fácil de ácido carboxílico vinílico.
Se empleó una nueva estrategia de contracción de anillos para la construcción final del núcleo heterocíclico.

Principales resultados:

Se completó con éxito la primera síntesis total de (+/-) -cartelina C.
La síntesis demostró una instalación eficiente de halógenos heteroaromáticos y una fracción sensible de beta-cloroenamida.
Una contracción de anillo única demostró ser efectiva, destacando su potencial para una síntesis heterocíclica más amplia.

Conclusiones:

La ruta de 10 pasos desarrollada representa un avance significativo en la síntesis de alcaloides complejos.
Las nuevas metodologías, en particular la contracción de anillos, ofrecen herramientas valiosas para futuras investigaciones de química heterocíclica.
Esta síntesis abre caminos para una mayor investigación sobre las actividades biológicas y los análogos estructurales de chartelline C.

Más Videos Relacionados

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

Synthesis of Biocompatible Liquid Crystal Elastomer Foams as Cell Scaffolds for 3D Spatial Cell Cultures

Synthesis of Biocompatible Liquid Crystal Elastomer Foams as Cell Scaffolds for 3D Spatial Cell Cultures

Published on: April 11, 2017

Videos de Conceptos Relacionados

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Conformations of Cyclohexane

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.