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

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

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%.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, N.I.H., Extramural

MeSH terms

  • Docosahexaenoic Acids / chemical synthesis
  • Docosahexaenoic Acids / chemistry
  • Fatty Acids, Unsaturated* / chemical synthesis
  • Fatty Acids, Unsaturated* / chemistry
  • Molecular Structure
  • Zinc / chemistry