Abstract: A total synthesis of (f)-brefeldin A has been achieved in 15 steps from trans-4-oxo-l, 2-cyclopentanedicarboxylic acid via the key intermediate 2c. Two distinct syntheses of 2 have been developed, leading to the trityl ether 2b and the methoxymethyl ether 2c. The former involves stereoselective conjugate addition of vinylalane 16 to hydroxy enone 4 and a surprisingly regioselective trityl ether isomerization. The latter synthesis employs the ...
