Polypropionates natural products continue to be an important and attractive area of research. A polypropionate is characterized by having aliphatic chains containing alternating methyl and hydroxy groups with distinct configurations. We have developed a reiterative epoxide-based methodology for the construction of polypropionates consisting of: epoxidation of an alkenol, epoxide ring opening, and generation of a new alkenol. Previous work in our laboratory used a remote TIPS protecting group, which was routinely incorporated into our approach towards polypropionates. Some limitations were encountered with this group, so we expanded this study to explore other protecting groups, including MEM and SEM. Interestingly, these protecting groups not only improved the versatility of our synthetic approach, but also showed a dramatic effect in the regioselectivity of the epoxide cleavage reaction of our 2-methyl-3,4-epoxy alcohols. These findings were further explored and extended with other epoxy alcohol diastereomers. Work supported by NIH SCORE (2S06GM-08102-29) and MARC (S06GM08102).

Effect of the remote protecting group in the cleavage reaction of 3,4-epoxy alcohols

243rd National Meeting (2012)

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