141902-99-0Relevant articles and documents
Absolute Configuration and Synthesis of 2-Hydroxy-2-(1-hydroxyethyl)-3-methyl-γ-butyrolactone, a Presumed Pheromone of Ithomiine Butterflies
Schulz, Stefan
, p. 829 - 834 (2007/10/02)
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 (3R)-enantiomers were synthesized by starting from rac- or (3S)-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 .In addition, the corresponding ketone, (2S,3R)-2-acetyl-2-hydroxy-3-methyl-γ-butyrolactone , could be identified as a new natural product from Prittwitzia hymaenea. Key Words: Pheromones / Ithomiinae / Ithomiolide / Keto lactone / Butterflies