Abstract
We report synthesis and characterization of dimer and oligomer acids from chaulmoogra oil. (R)-Methyl hydnocarpate (methyl ester of the major fatty acid component of chaulmoogra oil) was brominated to give threo-2,3-dibromocyclopentane-1-methyl undecanoate. Formation of two diastereoisomers, viz., threo-2(R),3(R)-dibromocyclopentane-1(R)-methyl undecanoate and threo-2(S),3(S)-dibromocyclopentane-(R)-1-methyl undecanoate, was observed. Dehydrobromination of bromo derivatives using alcoholic KOH gave a cyclopentadiene derivative as intermediate, which underwent Diels-Alder reaction to give dimer and oligomer fatty acids. The products were characterized by ultraviolet, direct exposure probe-mass spectroscopy, 1H nuclear magnetic resonance (NMR), and 13C NMR spectroscopic techniques.
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Malkar, N.B., Vaidya, A.A. & Kumar, V.G. Synthesis of dimer and oligomers from (R)-methyl hydnocarpate. J Amer Oil Chem Soc 77, 1101–1106 (2000). https://doi.org/10.1007/s11746-000-0173-7
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DOI: https://doi.org/10.1007/s11746-000-0173-7