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Related Concept Videos

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

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

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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.
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.3K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
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.
2.1K
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

5.6K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
5.6K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.9K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.3K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.3K

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Allocolchicines─Synthesis with Electro-organic Key Transformations.

Dennis Pollok1, Florian U Rausch1, Sebastian B Beil1

  • 1Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.

Organic Letters
|May 3, 2022
PubMed
Summary
This summary is machine-generated.

Meadow saffron compounds, colchicine and allocolchicines, show potential for cancer therapy. Researchers developed a sustainable five-step synthesis for these compounds, including the cancer drug ZD6126.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Cancer Therapeutics

Background:

  • Colchicine and allocolchicines, naturally found in meadow saffron, are investigated for their anticancer properties.
  • Existing synthesis methods may lack sustainability or efficiency.

Purpose of the Study:

  • To develop a concise and sustainable synthesis protocol for allocolchicines.
  • To enable access to key intermediates and derivatives for cancer drug development.

Main Methods:

  • A five-step synthetic route was designed.
  • Incorporation of up to two key electro-organic transformations.
  • Utilization of protecting groups for strategic synthesis.

Main Results:

  • Demonstrated a straightforward and sustainable synthesis of allocolchicines.
  • Successfully synthesized N-acetylcolchinol methyl ether.
  • Provided access to N-acetylcolchinol and the phosphate derivative ZD6126.

Conclusions:

  • The developed protocol offers an efficient pathway for producing potentially therapeutic allocolchicines.
  • This synthesis advances the accessibility of compounds like ZD6126 for cancer research.