Russian Chemical Bulletin p. 1595 - 1597 (1998)
Update date:2022-08-17
Topics:
Ishmuratov
Kharisov
Yakovleva
Botsman
Galeeva
Ishmuratova
Tolstikov
A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method comprises the conversion of the acid into undec-10-enyl acetate, shortening of its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecanoic acid), and a two-step transformation of the latter into the key intermediate, dec-9-yn-1-ol, by sequential bromination - dehydrobromination. The elimination of two HBr molecules from the dibromide is effectively performed using Bu1OK in the presence of dibenzo-18-crown-6 as the catalyst.
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