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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Michael R Gesinski¹, Kwanruthai Tadpetch, Scott D Rychnovsky

¹Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.

Organic Letters

|October 31, 2009

Summary

A new tandem reaction combines dimerization and macrocyclization using the Prins cyclization. This method efficiently creates complex, substituted tetrahydropyran macrocycles from various substrates.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

The Prins cyclization is a valuable reaction for forming tetrahydropyran rings.
Developing efficient methods for constructing complex macrocycles is crucial in synthetic chemistry.

Purpose of the Study:

To develop a novel tandem dimerization/macrocyclization reaction.
To synthesize highly substituted tetrahydropyran macrocycles.
To explore catalytic conditions for the reaction.

Main Methods:

Utilized a tandem reaction sequence involving Prins cyclization.
Employed rhenium(VII) catalysts for aromatic substrates under mild conditions.
Applied harsher Lewis acidic conditions for aliphatic substrates.
Investigated the use of both aldehydes and acetals as substrates.

Main Results:

Successfully developed a tandem dimerization/macrocyclization reaction.
Generated highly substituted dimeric tetrahydropyran macrocycles.
Demonstrated substrate scope including aromatic and aliphatic compounds.
Confirmed the viability of both aldehydes and acetals.

Conclusions:

The developed tandem reaction is an effective strategy for building molecular complexity.
The reaction provides access to valuable tetrahydropyran macrocyclic structures.
Catalyst choice is crucial for optimizing the reaction with different substrate types.