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1.
Pest Manag Sci ; 63(8): 809-14, 2007 Aug.
Article in English | MEDLINE | ID: mdl-17573681

ABSTRACT

A series of mono- and polyenehomobenzenes was synthesised by a highly regioselective palladium-catalysed allylic alkylation of substituted and unsubstituted benzylic Grignard reagents employing catalytic amounts of catalyst and tested for juvenile hormone activity on the fruit fly Drosophila virilis Sturtevant (Diptera: Drosophilidae), on an important agricultural pest species, the fall armyworm Spodoptera frugiperda JE Smith (Lepidoptera: Noctuidae), and on the map butterfly Araschnia levana L. (Lepidoptera: Nymphalidae). In D. virilis only polyenehomobenzenes with a geranyl chain and a methyl, methoxy or isopropyl group at the para position of the aromatic ring displayed significant juvenile hormonal activity at low doses. A monoenehomobenzene and polyenehomobenzenes with longer allylic chains or without a substituted aromatic ring were not active. In S. frugiperda and in A. levana, a mono-, a di- and a tetraene displayed juvenile hormonal activity. In the lepidopteran species, a trend for the necessity of a substitution at position 4 of the phenyl group for high juvenile hormonal activity was also found.


Subject(s)
Diterpenes/pharmacology , Drosophila/drug effects , Juvenile Hormones/analysis , Life Cycle Stages/drug effects , Spodoptera/drug effects , Animals , Diterpenes/chemistry , Moths/drug effects
2.
J Org Chem ; 67(4): 1167-70, 2002 Feb 22.
Article in English | MEDLINE | ID: mdl-11846658

ABSTRACT

A highly regioselective palladium-catalyzed alpha-alkylation of allylic bromides 1a,c-e and chloride 1b with substituted and unsubstituted benzylic Grignard reagents is reported. The resulting all-trans polyenehomobenzene derivatives were obtained in excellent yields and regioselectivity. These products were easily converted to abietane-type diterpenes (10-12) and tetracyclic polyprenoid compounds (13, 14) through a Lewis acid-promoted cascade polyene cyclization reaction.

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