Titanium (II)-based Z-reduction of alkynes. Syntheses of deuterium labelled linolenic and oleic acids and (3 E, 8 Z, 11 Z)-tetradeca-3, 8, 11-trienyl acetate, the sex …

NL Hungerford, W Kitching

Index: Hungerford, Natasha L.; Kitching, William Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 11 p. 1839 - 1858

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Citation Number: 31

Abstract

An operationally simple TiII-mediated, stereo-and regio-specific reduction of isolated, conjugated and methylene 'skipped'polyynes to the corresponding Z-polyenes in a one-pot procedure is described and applied inter alia to the syntheses of deuterium labelled linolenic and oleic acids. Final quenching with D2O (instead of H2O) results in regio-and stereo-specific Z-dideuteration of the alkyne. The synthesis of (3E, 8Z, 11Z)-tetradeca-3, 8, ...