In:
European Journal of Organic Chemistry, Wiley, Vol. 2008, No. 10 ( 2008-04), p. 1753-1758
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)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2008:10
DOI:
10.1002/ejoc.200700905
Language:
English
Publisher:
Wiley
Publication Date:
2008
detail.hit.zdb_id:
1475010-7
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