Tetrahedron letters

A new 3-methylidenepentane-1, 5-dianion synthon: synthesis of perhydropyrano [2, 3-b] pyrans and 1, 7-dioxaspiro [4.5] decanes

F Alonso, J Meléndez, M Yus

Index: Alonso, Francisco; Melendez, Jaisiel; Yus, Miguel Tetrahedron Letters, 2005 , vol. 46, # 38 p. 6519 - 6524

Full Text: HTML

Citation Number: 14

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 when subjected to successive hydroboration–oxidation and final oxidation, undergo ...