53170-97-1Relevant articles and documents
Clickable Vitamins as a New Tool to Track Vitamin A and Retinoic Acid in Immune Cells
Bos, Amelie V.,Erkelens, Martje N.,Koenders, Sebastiaan T.A.,van der Stelt, Mario,van Egmond, Marjolein,Mebius, Reina E.
, (2021/07/28)
The vitamin A derivative, retinoid acid (RA) is key player in guiding adaptive mucosal immune responses. However, data on the uptake and metabolism of vitamin A within human immune cells has remained largely elusive because retinoids are small, lipophilic
Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(-)-myrtenol nitrate
Bew, Sean P.,Hiatt-Gipson, Glyn D.,Mills, Graham P.,Reeves, Claire E.
supporting information, p. 1081 - 1095 (2016/07/06)
Here we report the chemoselective synthesis of several important, climate relevant isoprene nitrates using silver nitrate to mediate a 'halide for nitrate' substitution. Employing readily available starting materials, reagents and Horner-Wadsworth-Emmons chemistry the synthesis of easily separable, synthetically versatile 'key building blocks' (E)- and (Z)-3-methyl-4-chlorobut-2-en-1-ol as well as (E)- and (Z)-1-((2-methyl-4-bromobut-2-enyloxy)methyl)-4-methoxybenzene has been achieved using cheap, 'off the shelf' materials. Exploiting their reactivity we have studied their ability to undergo an 'allylic halide for allylic nitrate' substitution reaction which we demonstrate generates (E)- and (Z)-3-methyl-4-hydroxybut-2-enyl nitrate, and (E)- and (Z)-2-methyl-4-hydroxybut-2-enyl nitrates ('isoprene nitrates') in 66-80% overall yields. Using NOESY experiments the elucidation of the carbon-carbon double bond configuration within the purified isoprene nitrates has been established. Further exemplifying our 'halide for nitrate' substitution chemistry we outline the straightforward transformation of (1R,2S)-(-)-myrtenol bromide into the previously unknown monoterpene nitrate (1R,2S)-(-)-myrtenol nitrate.
New retinoid analogs from δ-pyronene, a natural synthon
Lambertin, Frederic,Wende, Martin,Quirin, Marie Jeanne,Taran, Martine,Delmond, Bernard
, p. 1489 - 1494 (2007/10/03)
δ-Pyronene (1), a readily available terpenic synthon, is an excellent raw material for the preparation of numerous terpenic intermediates. Original retinoid analogs such as 'iso'-retinyl acetate (5), 'iso'-retinal (6) and ethyl 'iso' retinoate (7), in which the cyclogeranyl moiety is functionalized in an unusual position, were prepared from δ-pyronene.