F. Alonso, J. Meléndez, T. Soler
Mar 6, 2006
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron
Abstract
Abstract 4-Phenylsulfanyl-2-(2-phenylsulfanylethyl)but-1-ene ( 2 ) has proved to be an appropriate and new 3-methylidenepentane-1,5-dianion synthon. The reaction of 2 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 3 . These diols undergo double intramolecular iodoetherification promoted by a silver salt, to furnish the corresponding 1,7-dioxaspiro[4.5]decanes ( 4 ) in very high yields. The oxidation of compounds 4 to the corresponding lactones is also studied.