Enantioselective total synthesis of 13-O-brefeldin A

An enantioselective route to the title compound, a heteroatom substituted close analogue of natural brefeldin A, is described. As a key step in the whole synthesis, concatenation of the lower chain and the cyclopentanone-upper chain moiety was achieved using a Rh-catalyzed Michael addition of a vinyl boronic acid to an enone, which effectively eliminated the problems encountered with the corresponding cuprate protocol and exemplified the potential of the strategy in synthesizing similar analogues.

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