Selective bis-hydride reduction of tosylmethyl-substituted tricyclic enones by lithium aluminium hydride synthesis of α-methylene cyclopentenoids

AAM Houwen-Claassen, AJH Klunder, B Zwanenburg

Index: Houwen-Claassen, Adrie A. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron, 1989 , vol. 45, # 22 p. 7149 - 7160

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Citation Number: 6

Abstract

On treatment with LAH the 4-tosylmethyl substituted exo-10-oxatricyclo [5.2. 1.02, 6] decadienones 1 and 3 undergo two consecutive, regioselective and stereospecific reductions. The first reduction constitutes an SN2′ displacement of the allylic tosyl group, the second a 1, 2-reduction of the resulting exo-cyclic enone to form the α-methylene cyclenols 7 and 8, respectively. These products are smoothly converted into α-methylene- ...