Termite trail attractants: New synthesis of racemic (E)-α-, (Z)-α- and β-bisabolenes

Article abstract of DOI:10.1080/00397919408010239

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.

Full text of DOI:10.1080/00397919408010239

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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Termite Trail Attractants: New
Syntheses of Racemic (E)-α-,
(Z)-α- and β-Bisabolenes
Laura Argenti a , Fabio Bellina a , Adriano Carpita a
Nicola Dell'Amico a & Renzo Rossi a
,
a Dipartimento di Chimica e Chimica , Industriale
- Università di Pisa , Via Risorgimento 35, I-56126,
Pisa, Italy
Published online: 23 Sep 2006.
To cite this article: Laura Argenti , Fabio Bellina , Adriano Carpita , Nicola Dell'Amico
& Renzo Rossi (1994) Termite Trail Attractants: New Syntheses of Racemic (E)-α-,
(Z)-α- and β-Bisabolenes, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 24:22, 3167-3188, DOI:
10.1080/00397919408010239
To link to this article: http://dx.doi.org/10.1080/00397919408010239
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