By introducing the strategy of intramolecular reductive coupling to construct the cyclopenta [b]benzofuran skeleton, the shortest and most efficient synthetic method hitherto was now established to rocaglamide 1 and its 2,3-di-epi analogue 3 in racemic form by Michael addition, SmI 2 -promoted intramolecular keto-ester coupling, amination of the ester intermediate, and reduction of carbonyl with Me 4 NBH(OAc) 3 . Several steps were highly stereoselective or even stereospec-