X‐Ray and 1 H‐NMR Configurational Assignment of Valofan (α‐Allphanoyl‐α‐allyl‐γ‐valerolactone) Diastereoisomers

X‐Ray and 1 H‐NMR Configurational Assignment of Valofan (α‐Allphanoyl‐α‐allyl‐γ‐valerolactone) Diastereoisomers

The two diastereoisomers of valofan were separated by semi‐preparative HPLC. The preferred solution conformation of the two diastereoisomer was established by 1 H‐NMR spectroscopy. The spectra could be interpreted in confirgurational terms. The configuration of the more lipophilic isomer was ascerta...

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Veröffentlicht in:Helvetica chimica acta 1984-09, Vol.67 (6), p.1662-1668
Hauptverfasser: Lauterwein, Jürgen, Alan Pinkerton, J., Wittekind, H. Harald, Testa, Bernard
Format: Artikel
Sprache:eng
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Zusammenfassung:The two diastereoisomers of valofan were separated by semi‐preparative HPLC. The preferred solution conformation of the two diastereoisomer was established by 1 H‐NMR spectroscopy. The spectra could be interpreted in confirgurational terms. The configuration of the more lipophilic isomer was ascertained bty X‐ray crystallography as r ‐2‐allophanoyl‐2‐allyl‐ t ‐4‐methylbutyrolactone.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19840670636