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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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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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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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Organocatalyst-controlled stereoselective head-to-tail macrocyclizations.

Jonas W Rackl1, Linus B Boll1, Helma Wennemers1

  • 1Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences (D-CHAB), ETH Zürich, Zürich, Switzerland.

Science (New York, N.Y.)
|February 26, 2026
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Summary
This summary is machine-generated.

This study introduces a new method for creating chiral macrocycles, essential for drug discovery. A peptide catalyst controls stereochemistry during head-to-tail macrocyclization, simplifying synthesis and ensuring predictable outcomes.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Chiral macrocycles are crucial for developing new pharmaceuticals.
  • Synthesizing chiral macrocycles is challenging, often requiring complex stereochemical installations in linear precursors.

Purpose of the Study:

  • To develop a practical and stereoselective method for synthesizing chiral macrocycles.
  • To demonstrate catalyst-controlled head-to-tail macrocyclization.

Main Methods:

  • Utilized a bifunctional peptide catalyst to template linear precursors.
  • Employed catalyst-controlled stereoselective head-to-tail macrocyclization.
  • Synthesized diverse macrocyclic lactones and lactams.

Main Results:

  • Achieved exquisite control over stereochemistry during macrocyclization.
  • Produced diverse 12- to 18-membered macrocyclic lactones and lactams from achiral precursors.
  • Demonstrated that the organocatalyst dictates stereochemical outcomes, even with chiral precursors.

Conclusions:

  • Developed a practical route to chiral macrocycles with predictable stereochemical outcomes.
  • The method simplifies the synthesis of complex chiral macrocyclic structures.
  • Highlighted utility by synthesizing the core of the natural product robotnikinin.