The [2, 3]-Wittig rearrangement of properly designated (E)-and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo-and erythro-selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds. Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (±)-oudemansin. Further, the high level of ...