1031812-80-2Relevant academic research and scientific papers
Total synthesis and biological activity of (±)-rocaglamide and its 2,3-di-epi analogue
Li, Hongsen,Fu,Wang,Li,Liu,Xie,Ma,Qin, Zhaohai
, p. 1753 - 1758 (2008)
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 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, 2008.
