Video Experimental Relacionado

Updated: Sep 3, 2025

Overexpression and Purification of Human Cis-prenyltransferase in Escherichia coli

Overexpression and Purification of Human Cis-prenyltransferase in Escherichia coli

Published on: August 3, 2017

Una síntesis concisa de pleurotina habilitada por una epimerización C-H no tradicional

John F Hoskin¹, Erik J Sorensen¹

¹Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|July 28, 2022

Resumen

Se desarrolló una síntesis eficiente de 8 pasos de un intermediario clave de pleurotina. Esta investigación avanza en la creación de productos naturales de benzoquinona con importantes propiedades anticancerígenas y antibióticas.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

La pleurotina y los productos naturales de benzoquinona relacionados exhiben potentes actividades anticancerígenas y antibióticas.
La síntesis de estas moléculas complejas es crucial para la investigación de la química medicinal.

Objetivo del estudio:

Describir una síntesis en 8 pasos de un intermediario pentacíclico conocido hacia el producto natural pleurotina.
Establecer una vía sintética para acceder a los productos naturales de benzoquinona biológicamente activos.

Principales métodos:

Fotoenolización intermolecular regionalizada y diastereoselectiva / cicloadición de Diels-Alder.
La epimerización C-H inducida por transferencia de átomos de hidrógeno por radicales alcohólicos.
Oxidación bencílica C-H que forma anillos.

Principales resultados:

Se logró una síntesis en 8 pasos de un intermediario pentacíclico.
La ruta sintética construyó con éxito el marco de carbono de la pleurotina con la estereoquímica correcta.
Oxepane 19 fue entregado como producto final.

Conclusiones:

La estrategia sintética desarrollada es eficaz para la construcción de esqueletos complejos de productos naturales.
Esta síntesis proporciona una vía valiosa para acceder a la pleurotina y sus análogos para una mayor evaluación biológica.

Más Videos Relacionados

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Published on: June 28, 2019

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Videos de Conceptos Relacionados

Sharpless Epoxidation

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...

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...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...