Tetrahedron

A direct synthesis of 1, 7-dioxaspiro [4.5] decanes from the new 3-methylidenepentane-1, 5-dianion synthon

F Alonso, J Meléndez, T Soler, M Yus

Index: Alonso, Francisco; Melendez, Jaisiel; Soler, Tatiana; Yus, Miguel Tetrahedron, 2006 , vol. 62, # 10 p. 2264 - 2277

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Citation Number: 18

Abstract

4-Phenylsulfanyl-2-(2-phenylsulfanylethyl) but-1-ene () has proved to be an appropriate and new 3-methylidenepentane-1, 5-dianion synthon. The reaction of with an excess of lithium powder and a catalytic amount of DTBB (2.5%) in the presence of a carbonyl compound in THF at 0° C, leads, after hydrolysis, to the expected methylidenic diols. These diols undergo double intramolecular iodoetherification promoted by a silver salt, to furnish the ...