Synthesis of tri‐, tetra‐, and penta‐deuterated forms of vitamin a

Harold Robert (Bob) III Bergen, Harold C. Furr, James A. Olson

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

The synthesis of 20,20,20‐trideutero, 14,20,20,20‐tetradeutero, 12,14,20,20,20‐pentadeutero, and 10,19,19,19‐tetradeutero analogs of retinoic acid ethyl ester and retinyl acetate, by a modified Wittig‐Horner synthesis, is described. Deuterium was introduced by base‐catalyzed exchange into appropriate intermediates. The 10,19,19,19‐2H4‐vitamin A, because of its high isotopic integrity (>98% 2H4), is the preferred analog for biological studies of vitamin A metabolism.

Original languageEnglish (US)
Pages (from-to)11-21
Number of pages11
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume25
Issue number1
DOIs
StatePublished - 1988
Externally publishedYes

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Keywords

  • 10,19,19,19‐H‐retinyl acetate
  • 12,14,20,20,20‐H‐retinyl acetate
  • 14,20,20,20‐H‐retinyl acetate
  • 20,20,20‐H‐retinyl acetate
  • deuterated retinyl acetate
  • Deuterated vitamin A analogues
  • retinoid synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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