Reactions of cyclopentanone, cyclohexanone, N-substituted pyrrolidin-3-one and piperidin-4-one, and tetrahydropyran-4-one with allyl bromide in the presence of zinc and ammonium chloride gave the corresponding geminal hydroxy allyl derivatives. Treatment of the latter with sodium periodate in the presence of sodium metabisulfite resulted in their oxidative cyclization with formation of oxa spirocyclic alcohols containing carbo-and heterocyclic fragments. Swern oxidation of the spiro alcohols afforded the corresponding ketones which were characterized as 2,4-dinitrophenylhydrazones.Spirocyclic derivatives of tetrahydrofuran attract interest as potential biologically active substances. For example, compounds I and II were isolated from plants [1,2], in particular from tea [3]. 8-Methyl-1-oxa-8-azaspiro[4.5]decan-3-one, 2,8-dimethyl-1-oxa-8-azaspiro[4.5]decan-3-one and their derivatives were reported to act as muscarinic cholinomimetics [4], i.e., their activity is analogous to that of such medical agents as Aceclidine and Pilocarpine. particular mercury(II) salts [5], lead(IV) acetate [8], and selenium(II) compounds [9], or expensive rhodium catalysts [11] were used, which may also be regarded as disadvantages.Taking into account the above stated and the results of our previous studies [12] on new heterocyclic spiro compounds, the goal of the present work was to develop a general procedure for the synthesis of spirocyclic 3-hydroxy-and 3-oxotetrahydrofuran derivatives containing carbo-and heterocyclic fragments. Interest in such compounds is determined by broad potential of their application in preparative organic synthesis due to the presence of functional groups. As starting compounds we used accessible carbo-and heterocyclic ketones, cyclopentanone (IIIa), cyclohexanone (IIIb), tert-butyl 3-oxopyrrolidine-1-carboxylate (IIIc), tert-butyl 3-oxopiperidine-1-carboxylate (IIId), tert-butyl-4-oxopiperidine-1-carboxylate (IIIe), and tetrahydropyran-4-one (IIIf). Ketones IIIa-IIIf fairly readily reacted with allyl bromide in the presence of zinc dust in tetrahydrofuran-saturated aqueous ammonium chloride over a period of 10-12 h at room temperature under vigorous stirring (TLC monitoring). As a result, the corresponding geminal allyl hydroxy derivatives IVa-IVf were formed in almost quantitative yield (Scheme 1); their structure was confirmed by elemental analyses, and IR, 1 H NMR, and mass spectra.