Video Experimental Relacionado

Updated: Oct 11, 2025

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Una síntesis total muy convergente de norhalichondrina B

K C Nicolaou¹, Saiyong Pan¹, Yogesh Shelke¹

¹Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, Texas 77005, United States.

Journal of the American Chemical Society

|December 1, 2021

Resumen

Los investigadores desarrollaron una nueva estrategia sintética para la norhalicondrina B, logrando la síntesis más corta hasta la fecha. Este enfoque convergente construye de manera eficiente complejos motivos cíclicos de éter, ofreciendo potencial para el desarrollo analógico.

Área de la Ciencia:

Química orgánica
Síntesis de productos naturales

Sus antecedentes:

La norhalichondrina B es un producto natural marino complejo con una actividad biológica significativa.
Las rutas sintéticas anteriores a la norhalichondrina B han sido largas y difíciles.

Objetivo del estudio:

Desarrollar una estrategia sintética altamente convergente y eficiente para la norhalicondrina B.
Establecer la ruta sintética más corta a la norhalichondrina B reportada hasta la fecha.

Principales métodos:

Una síntesis convergente que involucra dos fragmentos complejos.
Utilizó un enfoque inverso recientemente revelado para la síntesis de éter cíclico.
El paso clave fue la epimerización y la desprotección simultáneas.

Principales resultados:

Logró la síntesis total de norhalichondrina B a través de la ruta más corta.
Acoplado con éxito dos fragmentos complejos con alta eficiencia.
Demostró una táctica novedosa para el control estereocéntrico y la desprotección.

Conclusiones:

La estrategia desarrollada representa un enfoque sin precedentes dentro de la familia de las halichondrinas.
Este método ofrece una vía práctica para la síntesis de norhalichondrina B y sus análogos.
La estrategia tiene aplicaciones potenciales para la creación de diversos análogos de halichondrina naturales o diseñados.

Más Videos Relacionados

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

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...

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...

Radical Halogenation: Stereochemistry

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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.

Biosynthesis of Lipids

Biosynthesis of Lipids

Microbial membranes exhibit remarkable diversity in lipid composition, reflecting evolutionary adaptations to various environmental conditions. The three domains of life—Bacteria, Archaea, and Eukarya—synthesize membrane lipids through distinct biosynthetic pathways, leading to fundamental structural differences that impact membrane stability, function, and adaptability.Fatty Acid-Based Lipids in Bacteria and EukaryaBacteria and eukaryotes share a common fatty acid biosynthesis...