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Recebido em 22/8/97; aceito em 23/1/98In this paper we describe the reduction by NaBH 4 of some cyclopentanones containing an oxygenated function at the side chain position β β β β β to the carbonyl group, both in the presence and in the absence of CeCl 3 . Some suggestions for the rationalization of the results are discussed, considering the stereochemical course of the reactions.

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A epoxidação (H 2 O 2 , NaOH) de uma cicloeptenona-acetonilada forneceu um sesquiterpeno norguaiano bis-hidroxilado, através de uma seqüência inesperada de reações. Análise espectroscópica deste produto permitiu propor uma estrutura incluindo os grupos substituintes, porém a determinação tridimensional completa foi realizada por uma análise de difração de raio-X.The epoxidation (H 2 O 2 , NaOH) of an acetonyl-cycloheptenone derived from (R)-(-)-carvone gives a dihydroxy-nor-guaiane sesquiterpene by way of an interesting sequence of reactions promoted by the basic reaction conditions. Although the major product could be identified spectroscopically with respect to functional groups, its complete three dimensional structure was determined by X-ray mono-crystal diffraction studies.