Synthesis of New Medium- and Large- Sized Racemic and Chiral Lactones

Year 2018, Volume: 5 Issue: 2, 539 - 550, 01.01.2018

Hasniye Yaşa , Ayşe Sergüzel Yusufoğlu

https://doi.org/10.18596/jotcsa.372628

Cited By: 1

Abstract

Successive
reaction of long chain w-1, w-2, w-4 and w-5 hydroxycarboxylic acids 1a-1e with a cyanuric chloride (CC) and
triethylamine afforded the corresponding racemic lactones 2a-2e in high yields. Optically pure R lactones 4a-4e were
synthesized stereoselectively by porcine pancreas lipase-catalysed resolution
of racemic 2a-2e. The resolution
conditions were investigated, determined and optical rotations were measured.
The mentioned chiral lactones were synthesized by this method for the first
time. The obtained racemic and chiral lactones were analysed by NMR, IR, Mass,
optical rotation and C,H analysis.

Keywords

Synthesis, medium and large ring, lactone

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