The first synthesis of squamostanal-A (1), separated as a degradation
product of tetrahydrofuranic acetogenins, is described. Iodide 7, whic
h corresponds to the latent aldehyde moiety of 1, was prepared through
a 2-step sequence from 13-[tetrahydropyran-2'-yloxy]-2-tridecyn-1-ol
(5). The NaHMDS-based coupling reaction of 7 with gamma-lactone 8 gave
compound 9, which by a 3-step sequence, was coverted to 1.