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Title: ?POTENTIAL ANTIBACTERIAL AGENTS. PART III. SYNTHESIS OF 7-0XA-SPIRO [5, 9] PENTADECANE-1, 8, 13 TRIONE: A NOVEL MACROCYCLIC LACTONE
Authors: Shaheen A Husain, Tahira B Sarfaraz, Najma Murtaza, Naheed Sultana
Journal: Pakistan Journal of Scientific and Industrial Research (Series B: Biological Sciences)
Publisher: PCSIR Scientific Information Centre
Country: Pakistan
Year: 2000
Volume: 43
Issue: 3
Language: English
Keywords: Antibacterial agentMacrocyclic lactone2-morpholinomethyl cyclohaxanone2-oxa-spiro [5,9] pentadecane I8,13 trione.
In an attempt towards synthesis of intermediates (2a) 2-( l-cyanoethyl) cyclohexanone, (2b), 2-( l-nitroethyl) cyclo- hexanone reaction of morpholinomethyl cyclohexanone hydrochloride with CH)CN (or CH)N02) was undetaken. Instead of the two intermediates namely 2a, 2b the known compound 3 1-(l-oxo-2-hydroxycyclohexyl)-2-(2- oxocyclohexyl)-ethane was obtained. Oxidation of this compound and its LAH reduction product 4 1-(1,2- dihydroxycyclohexyl) -2-(2-hydroxycyclohexyl) ethane with CrO/Ac OH furnished a hitherto un-described com- pound 5, oxa-spiro [5,9] -pentadecane-l,8,13 trione. Its structure was established using spectroscopic techniques such as IR, HRIMS 'H-NMR, IlC-NMR etc. Antibacterial activities of the three synthesized compounds have been evaluated.
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