The chemistry of lauren-l-ene. II. Remote functionalization reactions of the laurenan-2-ols and the 1bH-laurenan-2-ols

Abstract

The course of the iodine/lead tetraacetate oxidation of the four alcohols laurenan-2β-ol(2), laurenan-2α-ol (3), 1βH-laurenan-2β-ol (4) and 1βH-laurenan-2α-ol (5) is described. Structural assignments have been made with the aid of ¹³C n.m.r. after ether ring opening and conversion into derivatives of lauren-1-ene (1). Where possible, the results of remote functionalization have been used to infer the preferred molecular conformation.