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

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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.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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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...
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Macrocyclization via remote meta-selective C-H olefination using a practical indolyl template.

Pengfei Zhang1, Zhiwei Jiang1, Zhoulong Fan2

  • 1College of Chemistry, State Key Laboratory of Elemento-organic Chemistry, Nankai University Tianjin 300071 China zjin@nankai.edu.cn.

Chemical Science
|August 11, 2023
PubMed
Summary

This study presents a new palladium-catalyzed method for synthesizing macrocyclic compounds via C-H activation. The efficient strategy enables the creation of macrolides, coumarins, and the antitumor drug belinostat.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Macrocyclic compound synthesis via C-H activation is challenging.
  • Developing efficient and versatile macrocyclization strategies is crucial.

Purpose of the Study:

  • To develop a novel palladium-catalyzed macrocyclization strategy.
  • To demonstrate the synthesis of diverse macrocyclic compounds including macrolides, coumarins, and the antitumor drug belinostat.
  • To explore the use of copper acetate and molecular oxygen as oxidants.

Main Methods:

  • Palladium-catalyzed remote meta-C-H olefination using an indolyl template.
  • Intramolecular and intermolecular C-H olefination reactions.
  • In situ monitoring using Fourier-transform infrared spectroscopy and ESI-MS.

Main Results:

  • An efficient macrocyclization strategy via Pd-catalyzed meta-C-H olefination was developed.
  • The method successfully synthesized macrolides and coumarins.
  • Intermolecular olefination yielded the antitumor drug belinostat from simple precursors.
  • Copper acetate and O2 replaced silver salts as oxidants.
  • A cyclopalladated intermediate was detected for the first time.

Conclusions:

  • The developed strategy offers an efficient route to diverse macrocyclic compounds.
  • This method provides a practical approach for synthesizing complex molecules, including pharmaceuticals.
  • The use of copper and oxygen as oxidants presents a greener alternative.