Titanium(II)-based Z-reduction of alkynes: stereo- and regio-specific Z-dideuteriation of conjugated and methylene-skipped ynes

Abstract

A Ti^II-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.