<br/>Dolabriferol is a marine polypropionate characterized by an unusual non-contiguous carbon skeleton, which possesses remarkable biological and pharmacological activity. Its structure consists of two related polypropionate subunits linked by an ester function. A polypropionate chain consists of an array of alternating methyl and hydroxy groups on an aliphatic chain with a particular configuration. We have developed a reiterative epoxide-based methodology for the construction of polypropionates that consists of a regioselective epoxide cleavage with an alkynyl aluminum reagent, reduction of the alkyne, and the stereoselective epoxidation of the resulting alkene. Employing this, we have engaged in a divergent/convergent synthesis of dolabriferol in which the same precursor is used for the elaboration of the two polypropionates fragments. We have synthesized the enantioselective key precursor containing the C3-C9 and C12-C18 segments of dolabriferol with the correct absolute configuration. From this key precursor, we have been able to synthesize the polypropionate acid moiety using our methodology. The details and recent advances towards the synthesis of dolabriferol target will be presented. Work supported by the NIH SCORE (2S06GM-08102-29) and NIH RISE (2R25GM061151-13) programs.

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Epoxide approach towards the synthesis of the polypropionate acid moiety of dolabriferol

249th National Meeting (2015)

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<br /> Epoxide approach towards the synthesis of the polypropionate acid moiety of dolabriferol