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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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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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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

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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
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Cycloaddition Reactions: Overview01:16

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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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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Programmed Polyene Cyclization Enabled by Chromophore Disruption.

Megan M Solans1, Vitalii S Basistyi1, James A Law1

  • 1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.

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|April 4, 2022
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Summary
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Researchers developed a novel polyene cyclization strategy using β-ionyl derivatives. This method efficiently synthesizes complex [4.4.1]-propellanes, improving regioselectivity and enabling new synthetic routes for natural products.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Natural Product Synthesis

Background:

  • Polyene cyclization is a key strategy in natural product synthesis.
  • Existing biomimetic tactics often suffer from limited regioselectivity.
  • Accessing complex polycyclic scaffolds like [4.4.1]-propellanes remains challenging.

Purpose of the Study:

  • To develop a new, regioselective polyene cyclization strategy.
  • To synthesize [4.4.1]-propellanes with improved efficiency and substrate scope.
  • To demonstrate the utility of the new strategy in natural product synthesis.

Main Methods:

  • Development of a novel polyene cyclization strategy exploiting β-ionyl derivatives.
  • Utilizing photoinduced deconjugation to generate a contrathermodynamic polyene.
  • Employing Heck bicyclization for the formation of [4.4.1]-propellanes.

Main Results:

  • The new cascade strategy achieves improved regioselectivity compared to existing methods.
  • The approach tolerates a wide range of electron-rich and electron-deficient (hetero)aryl groups.
  • Demonstrated successful diverted total synthesis of taxodione and salviasperanol.

Conclusions:

  • The developed strategy offers a powerful new route to [4.4.1]-propellanes.
  • This method overcomes limitations in regioselectivity and substrate scope of previous tactics.
  • The approach provides access to previously inaccessible isomeric abietane diterpenes.