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Abstract

OXIDATIVE FRAGMENTATION OF 1, 5-CYCLOOCTADIENE DERIVATIVE: A NEW ENTRY INTO 20-MEMBERED MACROCYCLE

M.M.V.Ramana*, Shrimant V. Rathod and M.S.Raje.

ABSTRACT

2-(1-Cyclooctenyl) ethanol was obtained from cyclooctanone by Reformatsky reaction followed by LAH reduction. 1,5- cyclooctadiene derivative i.e 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15, 16-hexadecahydrocyc-loocta[l,2-a:5,6-a']dioctene was synthesized by domino intermolecular alkylation and cycloalkylation from 2-(1- cyclooctenyl) ethanol. This 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16- hexa- decahydrocyclo-octa[l,2-a:5,6-a']dioctene, on oxidative fragmentation using Ruthenium oxide catalysed periodate oxidation afforded 20-membered cyclictetraketone.

Keywords: 1,5-cyclooctadiene, Oxidative fragmentation, 20- membered macrocycle.


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