Formation of Substituted Tetrahydropyrans through Oxetane Ring Opening: Application to the Synthesis of C1–C17 Fragment of Salinomycin

Formation of Substituted Tetrahydropyrans through Oxetane Ring Opening: Application to the Synthesis of C1–C17 Fragment of Salinomycin

The stereoselective synthesis of C1–C17 fragment of salinomycin is achieved. The strategy employs a desymmetrization approach and utilizes an intramolecular oxetane opening reaction with O-nucleophile to result in the tetrahydropyran skeleton as the key step.

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Veröffentlicht in:Organic letters 2014-02, Vol.16 (3), p.836-839
Hauptverfasser: Yadav, J. S, Singh, Vinay K, Srihari, P
Format: Artikel
Sprache:eng
Schlagworte:
Ethers, Cyclic - chemistry
Molecular Structure
Pyrans - chemistry
Stereoisomerism
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Zusammenfassung:The stereoselective synthesis of C1–C17 fragment of salinomycin is achieved. The strategy employs a desymmetrization approach and utilizes an intramolecular oxetane opening reaction with O-nucleophile to result in the tetrahydropyran skeleton as the key step.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403604u