Total synthesis of brefeldin A

PA Bartlett, FR Green III

Index: Bartlett,P.A.; Green,F.R. Journal of the American Chemical Society, 1978 , vol. 100, # 15 p. 4858 - 4865

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Citation Number: 75

Abstract

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 ...