Tellurium in organic synthesis: the enantioselective synthesis of the pheromone blend components of Mayetioladestructor, Drosophilamulleri and Contariniapisi

The components of the pheromone blend of Mayetioladestructor, Drosophilamulleri, and Contariniapisi were synthesized in high enantiomeric excess (99% ee) from a common enantiopure dianion prepared from an enantiopure hydroxytelluride.

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(S,E)-Tridec-10-en-2-yl acetateC15H28O2Ee = 99%[α]D22=+0.95 (c 1.02, CHCl3)Source of chirality: enantiopure hydroxytellurideAbsolute configuration: (2S)

(S,E)-Tridec-10-en-2-olC13H26OEe = 99%[α]D20=+6.8 (c 1.00, CHCl3)Source of chirality: enantiopure hydroxytellurideAbsolute configuration: (2S)

(2S,12S)-Tridecane-2,12-diyl diacetateC17H32O4Ee = 99%[α]D20=+2.0 (c 1.20, CHCl3)Source of chirality: enantiopure hydroxytellurideAbsolute configuration: (2S,12S)

(S)-Tridecan-2-yl acetateC15H30O2Ee = 99%[α]D20=+4.5 (c 1.00, hexane)Source of chirality: enantiopure hydroxytellurideAbsolute configuration: (2S)