?POTENTIAL ANTIBACTERIAL AGENTS. PART III. SYNTHESIS OF 7-0XA-SPIRO [5, 9] PENTADECANE-1, 8, 13 TRIONE: A NOVEL MACROCYCLIC LACTONE
Keywords:
Antibacterial agent, Macrocyclic lactone, 2-morpholinomethyl cyclohaxanone, 2-oxa-spiro [5,9] pentadecane I, 8,13 trione.Abstract
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.
