124753-55-5Relevant academic research and scientific papers
Enzymatic Resolutionof 2-Acyl-3-hydroxymethyl-4-butanolide and Preparation of Optically Active IM-2, the Autoregulator from Streptomyces sp. FRI-5
Mizuno, Kimihiro,Sakuda, Shohei,Nihira, Takuya,Yamada, Yasuhiro
, p. 10849 - 10858 (1994)
Racemic 2-acyl-3-hydroxymethyl-4-butanolides were resolved through a lipase-catalyzed acylation with acetic anhydride.Optically active forms of 2-butyryl-3-hydroxymethyl-4-butanolide 14 obtained were used to prepare enantiomers of IM-2 10, the autoregulator from Streptomyces sp.FRI-5.The absolute configuration of IM-2 was deduced to be (2R,3R,6R).
A modular and organocatalytic approach to γ-butyrolactone autoregulators from Streptomycetes
Elsner, Petteri,Jiang, Hao,Nielsen, Johanne B.,Pasi, Filippo,Jorgensen, Karl Anker
, p. 5827 - 5829 (2008)
A general synthesis of optically active γ-butyrolactone autoregulators is developed by a two-step sequence to assemble 2,3-trans-disubstituted butyrolactones in high yields and enantioselectivities; the scope of this reaction was elaborated by setting up a library of alkyl-substituted butyrolactones and the synthesis of the autoregulators IM-2 and VB-D. The Royal Society of Chemistry.
Organocatalytic approach for short asymmetric synthesis of (r)-paraconyl alcohol: Application to the total syntheses of IM-2, SCB2, and a-factor γ-butyrolactone autoregulators
Sarkale, Abhijeet M.,Kumar, Amit,Appayee, Chandrakumar
, p. 4167 - 4172 (2018)
(R)-Paraconyl alcohol is found to be a key intermediate for the syntheses of many γ-butyrolactone autoregulators. The chiral auxiliary approach and enzymatic resolution are the two common strategies employed so far in the literature for the asymmetric syn
