Enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-HEPTADECENE (cas 16369-12-3), the major component of the sex pheromone of the pear leaf midge, Dasineura pyri

Add time:08/03/2019    Source:sciencedirect.com

The first enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene 1, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri, has been achieved. The key steps include the (R,R)-BINOL/Ti(OiPr)4 catalyzed alkynylzinc addition to an unsaturated aldehyde, the ring-opening of the chiral epoxide with a Grignard reagent, and the partial reduction of an acetylenic diol ester to a (Z)-olefinic diol ester with hydrogen and P2-Ni.

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