European grapevine moth

Grapeb Lobesia botrana (European grapevine moth) E7,Z9-12 OAc EU 25,000 73,000... 

Dienes. Negishi and Abramovitch have found that reasonably hindered organoboranes are much more reactive to alkynyllithiums than an acetoxyl group is and have used this property for an efficient synthesis of (7E, 9Z)-dodecadien-1 -yl acetate, a sex pheromone of the European grapevine moth (equation I). 

A number of conjugated dienes have been identified as sex pheromones. Among these are (8 ,10 )-8,10-dodecadien-l-ol (475, Scheme 84) from the codling moth (Laspeyresia pomonella), (7 , 9Z)-7,9-dodecadien-1-yl acetate (490, Scheme 86) from the European grapevine moth (Lobesia botrana), ( )- and (Z)-9,ll-dodecadien-l-yl acetates (518a and 518b, respectively, see Scheme 90) from the red bollworm moth (Diparopsis castanea), and (10 , 12Z)-10,12-hexadecadien-l-ol (498, Scheme 87) from the silkworm moth (Bombyx mori). 

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