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Synthesis of Linoleic Acid with Chiral Isotopic Labelling at a Flanking and a Medial Allylic Methylene: the (8R,9Z,12Z)- and (11R,9Z,12Z)--Stereoisomers, and (Z)-Non-3-enal

DOI: 10.1039/P19920001929

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1929 - 1938 (1992)

Update date:2022-08-04

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Authors:

Crombie, LeslieCrombie, Leslie

Heavers, Andrew D.Heavers, Andrew D.

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Article abstract of DOI:10.1039/P19920001929

<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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Product name:(8S)-8-(p-tolylsulfonyloxy)-<8-(2)H>octanoic acid

Cas No:144401-72-9

144401-72-9

R&D Labs maybe for 144401-72-9

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