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).

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

BELLINA, FABIO;CARPITA, ADRIANO;ROSSI, RENZO
1996

Abstract

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).
Bellina, Fabio; Carpita, Adriano; Corradi, C.; Rossi, Renzo
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/205733
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