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Related Concept Videos

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones 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).
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Halogenation of Alkenes02:46

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.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Versatile solid-phase synthesis of chromenes resembling classical cannabinoids.

Dagmar C Kapeller1, Stefan Bräse

  • 1Karlsruhe Institute of Technology, Campus North, ComPlat, Eggenstein-Leopoldshafen, Germany.

ACS Combinatorial Science
|August 6, 2011
PubMed
Summary

A new solid-phase synthesis creates cannabinoid analogues in four steps. This method allows for combinatorial chemistry, producing a library of 20 compounds with good yields.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Classical cannabinoids are important natural products with diverse biological activities.
  • Developing efficient and versatile synthetic routes to cannabinoid analogues is crucial for drug discovery.
  • Existing synthetic methods may lack atom economy or combinatorial flexibility.

Purpose of the Study:

  • To develop a novel, atom-economic, solid-phase synthesis for classical cannabinoid analogues.
  • To enable combinatorial chemistry approaches for generating diverse cannabinoid structures.
  • To demonstrate the utility of the developed method by synthesizing a small library of compounds.

Main Methods:

  • A four-step synthesis involving domino oxa-Michael-aldol condensation, Wittig reaction/enol-ether formation, Diels-Alder cycloaddition, and cleavage.
  • Solid-phase synthesis approach allowing for purification and isolation of intermediates.
  • Combinatorial modification using varied enals/enones, Wittig salts, and dienophiles.

Main Results:

  • Successful assembly of tricyclic natural product analogues.
  • Demonstration of combinatorial chemistry at multiple stages.
  • Synthesis of a 20-member library of cannabinoid analogues.
  • Overall yields ranging from 10% to 60%.

Conclusions:

  • The described solid-phase approach provides an efficient and versatile route to classical cannabinoid analogues.
  • The method's design facilitates combinatorial synthesis, allowing for rapid generation of diverse molecular structures.
  • This approach holds promise for accelerating the discovery of novel cannabinoid-based therapeutics.