Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.
|Autori:||Argenti, L; Bellina, Fabio; Carpita, Adriano; Dellamico, N; Rossi, R.|
|Titolo:||TERMITE TRAIL ATTRACTANTS - NEW SYNTHESES OF RACEMIC (E)-ALPHA-BISABOLENE, (Z)-ALPHA-BISABOLENE AND BETA-BISABOLENE|
|Anno del prodotto:||1994|
|Digital Object Identifier (DOI):||10.1080/00397919408010239|
|Appare nelle tipologie:||1.1 Articolo in rivista|