Toward chemical libraries of annonaceous acetogenins: total synthesis of trilobacin

A synthetic route to 32 stereoisomers of a 10-carbon skeleton of bis-tetrahydrofuran (THT) acetogenins isolated from the Annonaceae family of plants was developed. The procedure, which was used to achieve the total synthesis of trilobacin for the first time, involves the generation and coupling of a phosphonium salt acting as a Wittig reagent and an aldehyde, oxidative cyclization with rhenium oxide and Mitsunobu inversion of alcohols.