Premium
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
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)
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom