Trail-following in termites: Stereoselective syntheses of (Z)-3-Dodecen- 1-OL, (3Z,6Z)-3,6-Dodecadien-1-OL and (3Z,6Z,8E)-3,6,8-dodecatrien-1-OL

Article abstract of DOI:10.1080/00397919408019053

(Z)-3-Dodecen-1-ol (4), a candidate trail-following semiochemical for several termite species, was synthetized by (Z)-stereoselective reduction of 3-dodecyn-1-ol (8). (3Z,6Z)-3,6-Dodecadien-1-ol (6), which is a structural analogue of 4, was prepared by a reaction sequence in which the key step was the cross-coupling between 5-(tert-butyldimethylsilyloxy)-2-pentyn-1-yl p- toluene-sulfonate (11) and 1-heptyne (12), in the presence of Cul, NaI and K₂CO₃. Finally, (3Z,6Z,8EZ)-3,6,8-dodecatrien-1-ol (3), which is a non- species-specific trail-following pheromone of termites, was prepared by a convergent synthesis in which compound 11 and (E)-3-hepten-1-yne (18) were used as key intermediates.

Full text of DOI:10.1080/00397919408019053

This article was downloaded by: [East Carolina University]
On: 26 August 2013, At: 01:19
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Trail-Following in Termites:
Stereoselective Syntheses
of (Z)-3-Dodecen-1-ol,
(3Z,6Z)-3,6-Dodecadien-1-
ol and (3Z,6Z,8E)-3,6,8-
Dodecatrien-1-ol
Laura Argenti a , Fabio Bellina a , Adriano Carpita a ,
Elena Rossi a b & Renzo Rossi a
a Dipartimento di Chimica e Chimica Industriale,
Università di Pisa, Via Risorgimento 35, I-56126,
Pisa, Italy
b Zambon Group, via Dovaro, I-36045, Lonigo
(Vicenza), Italy
Published online: 23 Sep 2006.
To cite this article: Laura Argenti , Fabio Bellina , Adriano Carpita , Elena Rossi &
Renzo Rossi (1994) Trail-Following in Termites: Stereoselective Syntheses of (Z)-3-
Dodecen-1-ol, (3Z,6Z)-3,6-Dodecadien-1-ol and (3Z,6Z,8E)-3,6,8-Dodecatrien-1-ol,
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 24:16, 2281-2297, DOI: 10.1080/00397919408019053
To link to this article: http://dx.doi.org/10.1080/00397919408019053
PLEASE SCROLL DOWN FOR ARTICLE

Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions