Total synthesis of demethyllavendamycin esters

Cardinal Scholar

Show simple item record Maharjan, Babu Raja en_US 2011-06-03T19:34:11Z 2011-06-03T19:34:11Z 1998 en_US 1998
dc.identifier LD2489.Z9 1998 .M34 en_US
dc.description.abstract 7-N-acetyldemethyllavendamycin butyl (11), pentyl (12) and hexyl (13) straight chain esters were synthesized via the Pictet-Spengler condensation of the desired tryptophan esters and 7-acetamido-2-formylquinoline-5,8-dione. Demethyllavandamycin butyl ester (14) was synthesized by the hydrolysis of 7-N-acetyldemethyllavendamycin butyl ester (11) with 70% mixture of sulfuric acid and water. The intermediate compound 8-hydroxy-2-methyl-5,7-dinitroquinoline (4) was synthesized by the nitration of 8-hydroxy-2-methylquinoline (3). Hydrogenation of compound 4 followed by acetylation resulted in 5,7-diacetamido-8-acetoxy-2-methylquinoline (6). Oxidation of compound 6 in the presence of potassium dichromate and acetic acid resulted in 7-acetamido-2-methylquinoline-5,8-dinoe (7). Further oxidation of compound 7 in the presence of selenium dioxide in 1,4-dioxane and a small quantity of water produced 7-acetamido-2-formylquinoline-5,8-dione (8). L-tryptophan butyl ester (15) was prepared by the neutralization of the commercially available hydrochloride salt of L-tryptophan butyl ester (18) with 14% ammonium hydroxide solution. L-tryptophan pentyl ester (16) and L-tryptophan hexyl ester (17) were prepared from L-tryptophan (19) according to the Fischer esterification reaction. The structures of compounds 15-17 were confirmed by 1H NMR Spectroscopy. Compounds 11-14 were identified by 1H NMR, IR, low and high resoluton mass spectroscopic methods. en_US
dc.description.sponsorship Department of Chemistry
dc.format.extent ix, 48 leaves : ill. ; 28 cm. en_US
dc.source Virtual Press en_US
dc.title Total synthesis of demethyllavendamycin esters en_US
dc.type Research paper (M.A.), 3 hrs. en_US Thesis (M.A.) en_US
dc.identifier.cardcat-url en_US

Files in this item

Files Size Format View

There are no files associated with this item.

This item appears in the following Collection(s)

  • Research Papers [5006]
    Research papers submitted to the Graduate School by Ball State University master's degree candidates in partial fulfillment of degree requirements.

Show simple item record

Search Cardinal Scholar


My Account