Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation

Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation

Stereoselective and parallel total syntheses of two possible diastereomers of (+)-sarcophytonolide C have been accomplished. Macrolactonization and transannular ring-closing metathesis (RCM) were the key transformations. Detailed comparisons of their 1H and 13C NMR data and specific rotation with th...

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Veröffentlicht in:Organic letters 2013-03, Vol.15 (5), p.1108-1111
Hauptverfasser: Takamura, Hiroyoshi, Iwamoto, Kohei, Nakao, Eiji, Kadota, Isao
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Anthozoa - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - isolation & purification
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes - isolation & purification
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Stereoisomerism
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Beschreibung
Zusammenfassung:Stereoselective and parallel total syntheses of two possible diastereomers of (+)-sarcophytonolide C have been accomplished. Macrolactonization and transannular ring-closing metathesis (RCM) were the key transformations. Detailed comparisons of their 1H and 13C NMR data and specific rotation with those of the natural product allowed the absolute configuration of (+)-sarcophytonolide C to be determined.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400157s