Video Experimental Relacionado
Updated: Jun 2, 2026
09:04
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Síntesis total de (±) cicloclavina y (±) -5-epi-cicloclavina
Filip R Petronijevic1, Peter Wipf
1Department of Chemistry and Center for Chemical Methodologies and Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Journal of the American Chemical Society
|April 27, 2011
Resumen
Los investigadores desarrollaron nuevas vías sintéticas para el alcaloide indol cicloclavina y su C(5) -epímero. Los pasos clave involucraron la rápida construcción de núcleos heterocíclicos utilizando reacciones de Diels-Alder y una formación única de bloques de construcción de cicloprop[c]indolina.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
- Síntesis de Productos Naturales.
Sus antecedentes:
- Los alcaloides indoles, como la cicloclavina, son una clase significativa de productos naturales con estructuras complejas.
- Las rutas sintéticas eficientes y estereoselectivas son cruciales para acceder a estos compuestos y sus análogos para su posterior estudio.
Objetivo del estudio:
- Diseñar nuevas estrategias sintéticas para la construcción de cicloclavina y su epímero no natural C(5) -epímero.
- Explorar la utilidad de las reacciones de Diels-Alder en la construcción del marco heterocíclico central de la cicloclavina.
Principales métodos:
- Se emplearon dos reacciones de Diels-Alder para el ensamblaje rápido de segmentos de núcleos heterocíclicos.
- Se utilizó una cicloadición intramolecular Diels-Alder de furanos en etapa tardía para la anulación del indol.
- Incorporó una cicloadición [4 + 2] intramolecular estereoselectiva con un dienófilo de metilenociclopropano para formar la fracción ciclopropana[c]indolina.
Principales resultados:
- Se establecieron con éxito nuevas rutas sintéticas para la cicloclavina y su epímero C ((5)).
- Demostró la eficiencia de las adiciones ciclónicas de Diels-Alder en la construcción de elementos estructurales clave.
- Generó el bloque de construcción característico de la ciclopropa[c]indolina estereoselectivamente.
Conclusiones:
- Las rutas sintéticas desarrolladas proporcionan un acceso eficiente a la cicloclavina y su epímero.
- El estudio pone de relieve el poder de las reacciones de Diels-Alder en la síntesis compleja de productos naturales.
- La metodología ofrece una plataforma valiosa para acceder a estructuras relacionadas de alcaloides indoles.
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Videos de Conceptos Relacionados
01:16Cycloaddition Reactions: Overview
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
02:33Stereoisomerism of Cyclic Compounds
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
02:05Prochirality
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...
02:37Disubstituted Cyclohexanes: cis-trans Isomerism
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
![[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F13097.jpg&w=3840&q=75)
01:24[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
01:27Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).