A TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene skipped poly-ynes to the corresponding Z-dideuterio polyenes in a one-pot procedure with D2O as deuterium source is described, and this methodology (using H2O) is applied to the synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex attractant of Scrobipalpuloides absoluta, a destructive pest of tomatoes.
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Hungerford et al. (1996) studied this question.
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