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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
Synthesis and Decomposition Reactions02:17

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition 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.
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
Predicting Products: SN1 vs. SN202:27

Predicting Products: SN1 vs. SN2

Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the substrate simultaneously as the leaving group departs, in SN1 reactions, the substrate first dissociates to give the carbocation intermediate. Various factors such as the structure of the substrate, the strength of the nucleophile, and the nature of the solvent promote one mechanism over the other.
With increased substitution on the alkyl halide,...

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.

Rebecca M Wilson1, Samuel J Danishefsky

  • 1Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.

The Journal of Organic Chemistry
|June 2, 2007
PubMed
Summary

Small molecule natural products (SMNPs) are valuable for discovering new drugs. Advanced chemical synthesis enables complex modifications to optimize SMNP potency and therapeutic index, accelerating pharmaceutical discovery.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • Small molecule natural products (SMNPs) are a rich source of biologically active compounds.
  • Traditional drug discovery methods often rely on screening natural product libraries.

Purpose of the Study:

  • To discuss the value of SMNPs in discovering active biological agents.
  • To highlight the synergy between natural product discovery and chemical synthesis.

Main Methods:

  • Exploration of advanced synthetic methodologies for modifying natural products.
  • Application of strategic bond disconnections and pattern recognition in synthetic planning.
  • Revisiting historical projects and presenting recent total syntheses of SMNPs.

Main Results:

  • Chemical synthesis significantly enhances the utility of SMNPs for drug discovery.
  • Modern synthetic capabilities allow for the creation of complex molecular structures.
  • Pattern recognition combined with advanced synthesis facilitates the development of novel therapeutics.

Conclusions:

  • The integration of SMNP-based discovery with sophisticated chemical synthesis is crucial for modern drug development.
  • Advances in synthetic chemistry enable the optimization of natural products for improved therapeutic properties.
  • Future drug discovery efforts will benefit from strategic approaches to natural product synthesis and modification.