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Absolute Configuration and Synthesis of 2-Hydroxy-2-(1-hydroxyethyl)-3-methyl-γ-butyrolactone, a Presumed Pheromone of Ithomiine Butterflies

✍ Scribed by Schulz, Stefan

Book ID: 102903169
Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 642 KB
Volume: 1992
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1992199201137

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✦ Synopsis

Abstract

2‐Hydroxy‐2‐(1‐hydroxyethyl)‐3‐methyl‐γ‐butyrolactone (1) is a constituent of scent glands of male ithomiine butterflies. All diastereomers and the respective (3__R__)‐enantiomers were synthesized by starting from rac‐ or (3__S__)‐3‐methyl‐γ‐butyrolactone 3. Their relative configurations were determined by difference NOE‐NMR spectroscopy or by X‐ray diffraction analysis. The absolute configuration of the natural product was determined by gas chromatography on a chiral stationary phase of the respective dioxolane derivatives. The natural lactone could be shown to be the (1′S,2__S__,3__R__)‐enantiomer [(1′S,2__S__,3__R__)‐1a, ithomiolide A]. In addition, the corresponding ketone, (2__S__,3__R__)‐2‐acetyl‐2‐hydroxy‐3‐methyl‐γ‐butyrolactone [(2__S__,3__R__)‐5a, ithomiolide B], could be identified as a new natural product from Prittwitzia hymaenea.

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