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Carbamate Series of Juvenoids: Variation of the O-alkyl substituent

✍ Scribed by Zdenêk Wimmer; David S̆aman; Václav Nêmec; Wittko Francke

Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
552 KB
Volume
77
Category
Article
ISSN
0018-019X

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✦ Synopsis

By changing the 0-alkyl substituents of the carbamate moiety of alkyl N-{2-{4-[(2-oxocyclohexyl)methyl]phenoxy}ethyl}carbamates and subsequent transformation of the 0x0 group in the cyclohexyl substituent, the juvenoids 1-20 were synthesized (Scheme). The methyl (la), propyl (%12), isopropyl (1>16), and prop-2ynylcarbamates (17-20) were subjected to biological screening on several non-related insect species (Tenebrio molitor, Galleria mellonellu, Dysdercus cinguiatus, and Pyrrhocoris apterus). Some of the juvenoids showed high biological activity and excellent selectivity with respect to target insect species (Table ).

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Direct conversion of Fmoc-protected amines into O-alkyl carbamates by the Mitsunobu reaction: a practical strategy for the solid-phase synthesis of carbamates
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