Abstract
AbstractBy 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, SmI2‐promoted intramolecular keto–ester coupling, amination of the ester intermediate, and reduction of carbonyl with Me4NBH(OAc)3. Several steps were highly stereoselective or even stereospecific. The bioassay results indicated that both 1 and 3 were much better repellents against Plutella xylostella than azadirachtin; the insecticidal activity of 1 was higher than that of azadirachtin against Pieris rapae, P. xylostella, Laphygma exigua, and Helicoverpa armigera, but that of 3 was lower.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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