Journal of the Chemical Society. Perkin transactions I p. 1929 - 1938 (1992)
Update date:2022-08-04
Topics:
Crombie, Leslie
Heavers, Andrew D.
<1-(2)H>-Oct-2-ynal is converted by fermenting bakers' yeast into (1S)-<1-(2)H>oct-2-yn-1-ol with an enantiomeric purity of >96percent as measured by Mosher's MTPA method.The alcohol, as its tosyl ester, was then converted by copper-catalysed coupling with the di-Grignard of dec-9-ynoic acid and catalytic semi-hydrogenation, into (11R)-<11-(2)H>linoleic acid having less than 2percent E-material and >95 atom percentD.Provision for (11S)-<11-(2)H>linoleic acid was made by configurational inversion of (1R)-<1-(2)H>oct-2-yn-1-ol using Mitsunobu chemistry.(8R)-<8-(2)H>Linoleic acid is made by a similar approach, the labelled chiral centre being formed on (8S)-8-hydroxy-<8-(2)H>octanoic acid (>96percent ee).Reaction of the corresponding tosate with lithium acetylide-ethylenediamine complex gave, with configurational inversion, (8R)-<8-(2)H>dec-9-ynoic acid, built into (8R)-<8-(2)H>linoleic acid.A degradative circuit is applied to estimate the extent of configurational inversion in the displacement.Mitsunobu inversion of the (8S)-8-hydroxy compound provides access to (8S)-<8-(2)H>linoleic acid. (Z)-Non-3-enal, a labile aldehyde from the enzymic degradation of linoleic acid, is made in <2,2-(2)H2>-labelled form by a synthesis which uses, as a key step, the reaction between triheptynylborane and deuteriodiazoacetic ester.
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