Oxidative fragmentation of 1, 5-cyclooctadiene derivative: A new entry into 14-membered macrocycle related to cembranoid group of diterpenoids

M.M.V.Ramana, Shrimant V. Rath

Abstract

14-Membered cyclictetraketone was synthesized by subjecting1,2,3,4,5,6,7,8,9,10-decahydrocycloocta[l,2-a:5,6- a']dipentene, a 1,5- cyclooctadiene derivative to oxidative fragmentation by Ruthenium oxide catalyzed periodate oxidation. The 1,5- cyclooctadiene derivative was synthesized by domino intermolecular alkylation and cycloalkylation of 2 -(1-cyclopentenyl) ethanol, which was obtained from cyclopentanone by Reformatsky reaction followed by LAH reduction. This 14-membered macrocycle has the carbocyclic frame work of cembrane, a 14- membered cyclic naturally occurring diterpene.