Synthesis of selected natural and nonnatural compounds

Abstract

Synthesis of natural products, especially molecules exhibiting useful biological and newlinepharmacological properties is one of the most challenging areas of the research in newlineorganic chemistry. The main purpose of this study was to develop convenient methods newlinefor the syntheses of bioactive natural products that are often isolated in very minute amounts from the natural resources. 4-Hydroxy-2(E)-nonenal (4-HNE) and 4-oxo-2(E)-nonenal (4-ONE) are the two lipid newlineperoxidation products found to be highly cytotoxic and genotoxic. The protein and newlineDNA adducts of 4-HNE and 4-ONE are commonly used as a biomarker for the occurance and /or the extent of lipid peroxidation. The author would like to present an efficient synthesis of these two molecules using Wittig reaction and Homer-Wardsworth-Emmons (HWE) reaction between glyoxal dimethyl acetal and the newlineph osph orane/ph osph onate. 4-Aryl-1,2,3,4-tetrahydroisoquinolines are the class of compounds that have potential to newlinebe used as antidepressants. Cherrylline and latifine are the two 4-Ary1-1,2,3,4- newlinetetrahydroisoquinoline derivatives that were tried to synthesize here. (+/-)-Cheryllin newlinedimethyl ether was successfully prepared via Curtius rearrangement of 343,4- newlinedimethoxypheny1)-3-(4-methoxyphenyepropanoic acid followed by the reduction and newlinePictate-Spenglar reaction. The extension of the similar methodology for the synthesis of newline(+/-) latifine dimethyl ether and asymmetric synthesis of Cherylline dimethyl ether was newlinealso tried. The naphthalene moiety (2-Hydroxy-7-methoxy-5-methyl-naphthalene-l-carboxylic acid) of the chromoprotein neocarzinostatin has been proposed to play an important role in its antitumor activity. Different attempts were made for the synthesis of above acid via number of routes. 7-(Benzyloxy)-4-methyl-2-acetonaphthone that was a key intermediate in the synthesis of this naphthalene moiety did not undergo Baeyer-Villiger oxidation.