Video Experimental Relacionado

Updated: May 4, 2026

Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks

Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks

Published on: November 25, 2015

Una síntesis de 15 pasos de (+) -rianodol

Kangway V Chuang¹, Chen Xu¹, Sarah E Reisman²

¹Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.

Science (New York, N.Y.)

|August 27, 2016

Resumen

(+) - Ryanodol, un diterpenoide complejo, fue sintetizado en 15 pasos. Este método eficiente para sintetizar moduladores de receptores de ryanodine utiliza reacciones clave para la construcción rápida del marco de carbono y la instalación de oxígeno.

Área de la Ciencia:

Química orgánica
Biología molecular
La biofísica

Sus antecedentes:

(+) - Ryanodine y (+) - ryanodol son diterpenoides complejos que regulan la liberación de iones de calcio intracelular a través de los receptores de ryanodine.
Los receptores de ryanodina son cruciales para el acoplamiento de la excitación y la contracción muscular y la transmisión sináptica.
Las modificaciones estructurales de estos diterpenoides pueden afectar su afinidad de unión y selectividad para las isoformas de los receptores de ryanodina.

Objetivo del estudio:

Desarrollar una síntesis química concisa y eficiente para el (+) -rianodol.
Explorar construcciones estratégicas de enlaces C-O para agilizar la síntesis de terpenos polihidroxilados.

Principales métodos:

Una síntesis en quince pasos de (+) -rianodol a partir de (S) -pulegona.
Utilizó una reacción de Pauson-Khand para el ensamblaje rápido del marco de carbono.
Se utiliza oxidación mediada por SeO2 para la instalación simultánea de tres átomos de oxígeno.

Principales resultados:

Se sintetizó con éxito (+) -rianodol en un número significativamente reducido de pasos.
Demostró la eficiencia de la reacción de Pauson-Khand y la oxidación mediada por SeO2 en esta síntesis.
Destacó la importancia de las formaciones estratégicas de bonos C-O.

Conclusiones:

Se ha logrado una síntesis rápida y eficiente de (+) -rianodol.
Esta ruta sintética minimiza la necesidad de proteger grupos y ajustes redox.
La estrategia es aplicable a la síntesis de otros terpenos polihidroxilados.

Más Videos Relacionados

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

Videos de Conceptos Relacionados

Synthesis and Decomposition Reactions

Synthesis and Decomposition Reactions

Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes.

Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Acid-Catalyzed Aldol Addition Reaction

Acid-Catalyzed Aldol Addition Reaction

The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are...

Leveling Effect

Leveling Effect

In acid-base chemistry, the leveling effect refers to the limitation imposed by the solvent on the strength of acids and bases in solution. When a base stronger than the solvent's conjugate base is used, it deprotonates the solvent until the base is entirely consumed, making it ineffective against weaker acids. Conversely, an acid stronger than the solvent's conjugate acid protonates the solvent until the acid is depleted, rendering it ineffective against weaker bases. Essentially, the...