Termite Trail Attractants: New Syntheses of Racemic (E)-α-, (Z)-α- andβ-Bisabolenes
- 1 December 1994
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 24 (22) , 3167-3188
- https://doi.org/10.1080/00397919408010239
Abstract
Racemic (E)-α-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)-α-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 β-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.Keywords
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