A Unified Synthetic Approach to Polyketides Having Both Skeletal and Stereochemical Diversity

A Unified Synthetic Approach to Polyketides Having Both Skeletal and Stereochemical Diversity

An efficient systematic approach to the diversity-oriented synthesis of polyketides has been developed to provide both skeletal and stereochemical diversity. Each synthetic intermediate is also a desired polyketide fragment and no protecting group manipulations are required. A first-generation synth...

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Veröffentlicht in:Organic letters 2007-05, Vol.9 (10), p.1895-1898
Hauptverfasser: Shang, Shiying, Iwadare, Hayato, Macks, Daniel E, Ambrosini, Lisa M, Tan, Derek S
Format: Artikel
Sprache:eng
Schlagworte:
Carbon - chemistry
Epoxy Compounds - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Methylation
Molecular Structure
Stereoisomerism
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Zusammenfassung:An efficient systematic approach to the diversity-oriented synthesis of polyketides has been developed to provide both skeletal and stereochemical diversity. Each synthetic intermediate is also a desired polyketide fragment and no protecting group manipulations are required. A first-generation synthesis provides a 74-membered polyketide library comprising six different skeletal classes, each in one to five steps from propargylic alcohol precursors. A study of epoxyol opening reactions revealed unusual reactivity trends based on epoxide configuration.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070405p