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Related Concept Videos

Preparation of Epoxides03:00

Preparation of Epoxides

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...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
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.
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).
Pyruvate Oxidation01:15

Pyruvate Oxidation

After glycolysis, the charged pyruvate molecules enter the mitochondria via active transport and undergo three enzymatic reactions. These reactions ensure that pyruvate can enter the next metabolic pathway so that energy stored in the pyruvate molecules can be harnessed by the cells.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Yeast-mediated xanthone synthesis through oxidative intramolecular cyclization.

Yann Fromentin1, Philippe Grellier, Jean Duplex Wansi

  • 1Unité Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS-MNHN, 57, Rue Cuvier, CP54, 75005, Paris, France.

Organic Letters
|September 19, 2012
PubMed
Summary

Researchers explored modifying natural benzoylphloroglucinol products using yeast. This study discovered a novel yeast-catalyzed oxidation yielding new oxy-guttiferone A and norathyriol compounds.

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Area of Science:

  • Natural Product Chemistry
  • Biotechnology
  • Organic Chemistry

Background:

  • Benzoylphloroglucinol derivatives are natural products with diverse biological activities.
  • Structural modifications can modulate these biological activities.
  • Exploring biotransformation offers a pathway for novel compound discovery.

Purpose of the Study:

  • To investigate the biotransformation of guttiferone A and maclurin.
  • To identify microorganism strains capable of modifying these compounds.
  • To discover novel derivatives with potentially altered biological activities.

Main Methods:

  • Employed a combinatorial approach for screening microorganism strains.
  • Utilized yeast for biotransformation experiments.
  • Analyzed products using chemical and spectroscopic methods.

Main Results:

  • Identified a novel yeast-catalyzed oxidation pathway.
  • Successfully synthesized a new oxy-guttiferone A derivative.
  • Successfully synthesized norathyriol.

Conclusions:

  • Yeast-mediated biotransformation is effective for modifying benzoylphloroglucinol derivatives.
  • This study yielded previously undescribed compounds.
  • The findings open avenues for exploring new bioactive natural products.