Identification of a nitrogen-containing compound in flowers of aglaia odorata lour. and synthesis of 1-Methyl-2-piperidone derivatives

Abstract

In this research work, the nitrogen-containing compound from the methanol extract of the ground dried flowers of Aglaia odorata Lour. was identified as 4-hydoxy-N-methyl-L-proline according to its physical and chemical properties including spectroscopic data and X-ray crystallographic data. It was the first report of this compound in Aglaia species. Moreover, 1, 2-0-isopropylidene-∝-D-xylofuranose was prepared from ∝-D-glucose. The cis-hydroxyl group of ∝-D-glucose was protected to form acetals and furanose ring as 1, 2:5 , 6-di-0-isopropylidene-∝-D-glucofuranose. An acetal ring was hydrolyzed at 5,6-position of carbon to obtain alcohol product which was converted to aldehyde by periodate oxidation and was reduced to yield 1, 2-0-isopropylidene-∝-D-xylofuranose. To prepare the 3-deoxygenated analog, the 3-hydroxy group of 1, 2:5, 6-di-0-isopropylidene-∝-D-glucofuranose was first converced to 0-alkyl-S-methyldithiocarbonate (xanthate ester) and directly reduced with TBTH to obtain the 3-deoxygenated product after chromatographic purification. Then, hydrolysis and periodate oxidation gave the final product as 1, 2-0-isopropylidene-3-deoxy-∝-D-erythropentodialdofuranose. In this work, the synthesis of 1-methyl-2-piperidone derivative was not accomplished by these routes due to failure in purification of some intermediate. However, the spectroscopic data of all synthesized compounds were not previously reported.