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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Preparation of Epoxides03:00

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

5.0K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Oxidative Cyclization in Natural Product Biosynthesis.

Man-Cheng Tang1, Yi Zou1, Kenji Watanabe2

  • 1Department of Chemical and Biomolecular Engineering, and Department of Chemistry and Biochemistry, University of California, Los Angeles , 420 Westwood Plaza, Los Angeles, California 90095, United States.

Chemical Reviews
|December 13, 2016
PubMed
Summary
This summary is machine-generated.

Nature employs oxidative cyclizations to build complex molecules from simple precursors. This review explores redox chemistry strategies, including radical and nonradical pathways, used in natural product biosynthesis.

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Natural Product Biosynthesis

Background:

  • Oxidative cyclizations are crucial in natural product biosynthesis, enabling the formation of complex molecular scaffolds.
  • These transformations from acyclic precursors to cyclic products yield structural rigidity and biological activity.
  • Dramatic structural alterations in natural products often arise from oxidative cyclization events.

Purpose of the Study:

  • To review the diverse strategies utilized by nature for creating new intra(inter)molecular bonds through redox chemistry.
  • To provide a comprehensive overview of both oxidation- and reduction-enabled cyclization mechanisms, with a focus on oxidative pathways.
  • To highlight the role of specific enzymes and cofactors in driving these complex transformations.

Main Methods:

  • Discussion of radical cyclizations catalyzed by P450, nonheme iron, alpha-ketoglutarate (α-KG)-dependent oxygenases, and radical S-adenosylmethionine (SAM) enzymes.
  • Examination of nonradical cyclizations facilitated by flavin-dependent monooxygenases and NAD(P)H-dependent reductases.
  • Analysis of oxidative installations of epoxides and halogens as 'disappearing' reactive handles and oxidative rearrangements of ring systems.

Main Results:

  • Illustrates the use of molecular oxygen and S-adenosylmethionine in one-electron manifolds for forging bonds at unactivated sites.
  • Demonstrates the application of two-electron manifolds in initiating cyclization reactions via flavin and NAD(P)H-dependent enzymes.
  • Covers oxidative ring contractions and expansions as significant biosynthetic rearrangements.

Conclusions:

  • Nature utilizes a sophisticated array of redox strategies for oxidative cyclization in natural product biosynthesis.
  • Enzymatic catalysis, involving both radical and nonradical pathways, is key to forming complex molecular architectures.
  • Understanding these mechanisms provides insights into biosynthetic pathways and potential synthetic applications.