DOI: 10.1007/bf02537333. Preparation of methylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐15,16‐d2 and methylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐6,6,7,7‐d4

Preparation of methylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐15,16‐d2 and methylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐6,6,7,7‐d4

10.1007/bf02537333

Crossref journal-article

Wiley

Lipids (311)

Abstract

AbstractMethylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐15,16‐d2 was obtained from Wittig coupling of methyl 12‐oxo‐cis‐9‐dodecenoate,18, and 3,4‐dideutero‐cis‐3‐hexenyltriphenylphosphonium bromide,16. Compound18 was obtained by periodic acid oxidation of methyl 12,13‐dihydroxy‐cis‐9‐octadecenoate,17, obtained fromVernonia oil. Compound18 also was synthesized from methyl oleate as the starting material. The deuterated fragment,16, was prepared from 3‐hexynol and using Lindlar's catalyst and deuterium gas to introduce the deuterium atoms.Methylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐6,6,7,7‐d4 was prepared by Wittig coupling of 3,6‐nonadienyltriphenylphosphonium iodide,5, with methyl 9‐oxononanoate‐6,6,7,7‐d4,11. Deuterium atoms were introduced during the synthesis of11 from 3‐butynol and 5‐bromopentanoic acid with deuterium gas in the presence of [Ph3P]3‐RhCl. For the preparation of5, the 3,6‐nonadiynol intermediate was reduced to 3,6‐nonadienol with P‐2 Nickel and hydrogen.The final products were separated from isomers formed during the synthetic sequences by silver resin chromatography.

Bibliography

Rakoff, H. (1988). Preparation of methylcisâ9,cisâ12,cisâ15âoctadecatrienoateâ15,16âd2 and methylcisâ9,cisâ12,cisâ15âoctadecatrienoateâ6,6,7,7âd4. Lipids, 23(4), 280â285. Portico.

Authors 1

Henry Rakoff (first)

References 15 Referenced 16

{'key': 'e_1_2_1_2_1', 'first-page': '99', 'volume-title': 'Geometrical and Positional Fatty Acid Isomers', 'author': 'Emken E.A.', 'year': '1979'} / Geometrical and Positional Fatty Acid Isomers by Emken E.A. (1979)
10.1007/BF02534378
10.1002/jlcr.2580150130
10.1002/jlcr.2580190105
10.1016/0009-3084(84)90017-3
6.Brown C.A. andAhuja V.K.(1973)J. Chem. Soc. Chem. Commun. 553–554. (10.1039/C39730000553)
10.1271/bbb1961.41.1481
8.Corey E.J. andSuggs J.W.(1975)Tetrahedon Lett. 2647–2650. (10.1016/S0040-4039(00)75204-X)
10.1007/BF02672190
10.1080/00397917908066695
10.1007/BF02679784
12.Stowell J.C. andKeith D.R.(1979)Synthesis 132–133. (10.1055/s-1979-28589)
10.1016/0163-7827(85)90006-2
10.1016/0163-7827(82)90010-8
10.1007/BF02667269

Dates

Type	When
Created	18 years, 9 months ago (Nov. 29, 2006, 1:28 a.m.)
Deposited	1 year, 11 months ago (Sept. 29, 2023, 3:21 a.m.)
Indexed	1 year, 11 months ago (Sept. 30, 2023, 2:10 p.m.)
Issued	37 years, 5 months ago (April 1, 1988)
Published	37 years, 5 months ago (April 1, 1988)
Published Online	37 years, 5 months ago (April 1, 1988)
Published Print	37 years, 5 months ago (April 1, 1988)

Funders 0

None

BibTeX

@article{Rakoff_1988, title={Preparation of methylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐15,16‐d2 and methylcis‐9,cis‐12,cis‐15‐octadecatrienoate‐6,6,7,7‐d4}, volume={23}, ISSN={1558-9307}, url={http://dx.doi.org/10.1007/bf02537333}, DOI={10.1007/bf02537333}, number={4}, journal={Lipids}, publisher={Wiley}, author={Rakoff, Henry}, year={1988}, month=apr, pages={280–285} }

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