60468-23-7Relevant articles and documents
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
Bellina, Fabio,Carpita, Adriano,Corradi, Chiara,Rossi, Renzo
, p. 3297 - 3316 (2007/10/03)
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).
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
Argenti,Bellina,Carpita,Rossi,Rossi
, p. 2281 - 2297 (2007/10/02)
(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.