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Total Synthesis and Biological Activity of (±)‐Rocaglamide and Its 2,3‐Di‐ epi Analogue
Author(s) -
Li Hongsen,
Fu B.,
Wang M. A.,
Li N.,
Liu W. J.,
Xie Z. Q.,
Ma Y. Q.,
Qin Zhaohai
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700905
Subject(s) - chemistry , intramolecular force , azadirachtin , reductive amination , plutella , stereochemistry , total synthesis , stereoselectivity , benzofuran , stereospecificity , stereocenter , acetogenin , organic chemistry , enantioselective synthesis , botany , pesticide , lepidoptera genitalia , annonaceae , agronomy , biology , catalysis
Abstract 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 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)