Synthetic routes to the stereoisomers of 2,4-dimethylpentane-1,5-diol derivatives

Five different routes to every stereoisomer of non-symmetric derivatives of 2,4-dimethylpentanedioic acid and/or of O-monoprotected 2,4-dimethylpentane-1,5-diols, which are common building blocks for the total synthesis of many polypropionates, have been investigated. Alkylation of the lithium enolate of N-propanoylpseudoephedrine turned out to be the most appropriate method, in connection with the synthesis of fragment C1–C5 of amphidinolide K.