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. 2024 May 15;22(19):3951-3954.
doi: 10.1039/d4ob00536h.

A gram-scale synthesis of very-long chain polyunsaturated fatty acids (VLC-PUFAs)

Changqing Song  1 , Alex Wade  1 , Jon D Rainier  1
Affiliations

A gram-scale synthesis of very-long chain polyunsaturated fatty acids (VLC-PUFAs)

Changqing Song et al. Org Biomol Chem. .

Abstract

This manuscript describes our third generation, gram-scale synthesis of very long chain-polyunsaturated fatty acids (VLC-PUFAs), a unique and increasingly important class of lipids. Critical to this work and what makes it different from our previous approach to this family was the avoidance of oxidation sequences. Central to accomplishing this involved the use of a Negishi coupling reaction between the acid chloride derived from DHA and a saturated alkyl zinc reaction. Overall, the general approach required 6 synthetic transformations from DHA and was accomplished with an overall yield of 40%.

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Conflict of interest statement

Conflicts of interest

There are no conflicts of interest to declare.

Figures

Scheme 1
Scheme 1
Previous synthesis of VLC-PUFA 32:6 n-3.
Scheme 2
Scheme 2
DHA acid chloride Negishi coupling to VLC-PUFAs.
Scheme 3
Scheme 3
Completion of the gram scale synthesis of 32:6 n-3.
Scheme 4
Scheme 4
Synthesis of VLC-PUFA: 34:6 n-3.
See this image and copyright information in PMC

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