The stereoselective total synthesis of the non‐contiguous polypropionate dolabriferol has been accomplished in 17 steps, by an approach that is both divergent and convergent. The key reactions involved are enantioselective cross‐aldol coupling, aldol dimerisation of propionaldehyde, Sharpless asymmetric epoxidation, regioselective epoxide opening and Yamaguchi esterification. The effects of the protecting groups on the alcohol substrate on differential reactivity in Yamaguchi esterification were noteworthy.
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