Candidate trail attractants of Reticultermes lucifugus: Stereoselective syntheses of (3Z, 6E, 8E)- (3Z, 6E, 8Z)- and (3Z, 6Z, 8Z)-3,6,8-dodecatrien-1-ol

Article abstract of DOI:10.1080/00397919608004640

Stereoselective syntheses on a gram scale of (3Z,6E,8E)-, (3Z,6E,8Z)- and (3Z,6Z,8Z)-3,6,8-dodecatrien-1-ol, 8, 9 and 10, respectively, are described. A key step of the synthesis of 8 consisted of a copper-mediated coupling reaction between 4-(2-tetrahydropyranyloxy)-1-butynylmagnesium bromide (15) and the mesyl ester of (2E,4E)-2,4-octadien-1-ol (14). A similar copper-mediated reaction between 15 and the mesyl ester of (E)-2-octen-4-yn-1-ol (19) was used to construct the C-12 carbon skeleton of 9. On the other hand, the synthesis of 10 was based on a palladium-promoted reaction between (Z)-1-bromo-1-pentene (23) and the organozinc bromide derived from 3,6-heptadiyn-1-yl acetate (27).

Full text of DOI:10.1080/00397919608004640

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Synthetic Communications: An
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Candidate Trail Attractants
of Reticultermes lucifugus:
Stereoselective Syntheses
of (3Z, 6E, BE)-(3Z, 6E, 8Z)-
and (3Z, 6Z, 8Z)-3,6,8 -
Dodecatrien-1-OL1
Fabio Bellina a , Adriano Carpita a , Chiara Corradi a
& Renzo Rossi a
a Dipartimento di Chimica e Chimica Industrials ,
Università di Pisa , Via Risorgimento 35, I-56126,
Pisa, Italy
Published online: 21 Aug 2006.
To cite this article: Fabio Bellina , Adriano Carpita , Chiara Corradi & Renzo Rossi
(1996) Candidate Trail Attractants of Reticultermes lucifugus: Stereoselective
Syntheses of (3Z, 6E, BE)-(3Z, 6E, 8Z)-and (3Z, 6Z, 8Z)-3,6,8 -Dodecatrien-1-OL1 ,
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 26:17, 3297-3316, DOI: 10.1080/00397919608004640
To link to this article: http://dx.doi.org/10.1080/00397919608004640
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