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A new synthesis of (+)-brefeldin A is reported via Padwa allenylsulfone [3 + 2]-cycloadditive elimination. Cycloadduct 13 was initially elaborated into iodide 27, which, following treatment with Zn, gave aldehyde 28 whose C(9) stereocenter was epimerized. Further elaboration into enoate 38 and Julia-Kocienski olefination with 5 subsequently afforded 39, which was deprotected at C(1) and O(15). Yamaguchi macrolactonization of the seco-acid thereafter afforded a macrocycle that underwent O-desilylation and inversion at C(4) to give (+)-brefeldin A following deprotection.

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Total Synthesis of the Antitumor Macrolides, (+)-Brefeldin A and 4-Epi-Brefeldin A from <scp>d</scp>-Glucose: Use of the Padwa Anionic Allenylsulfone [3 + 2]-Cycloadditive Elimination To Construct Trans-Configured Chiral Cyclopentane Systems

Total Synthesis of the Antitumor Macrolides, (+)-Brefeldin A and 4-Epi-Brefeldin A from d-Glucose: Use of the Padwa Anionic Allenylsulfone [3 + 2]-Cycloadditive Elimination To Construct Trans-Configured Chiral Cyclopentane Systems