Tetrahedron

Terpenoids—XCVII: Base catalysed reactions with n-lithioethylene-diamine

BN Joshi, KK Chakravarti, SC Bhattacharyya

Index: Joshi,B.N. et al. Tetrahedron, 1967 , vol. 23, p. 1251 - 1257

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Abstract

Reaction of N-lithioethylenediamine on the 11-membered monocyclic sesquiterpenoids zerumbone (I) and zerumbol (II) has been studied. Zerumbone undergoes polymerization in the presence of the reagent whereas zerumbol via transannular cyclization-oxidation is converted to the bicyclic ketone, 2-keto-Δ5; 6, 4; 11-bicyclo (6: 3: 0) undecane (VII). Its structure has been rigorously established by chemical degradation and spectral studies.