86941-88-0Relevant academic research and scientific papers
Biomimetic synthesis of nudicaulins i and II, yellow pigments from the Iceland poppy: Papaver nudicaule
Devlin, Rory,Sperry, Jonathan
supporting information, p. 13594 - 13597 (2019/11/14)
Indole and the anthocyanin orientalin proceed through a unique cascade sequence that leads to nudicaulins I and II in 92% yield. This biomimetic synthesis confirms the biosynthesis proposal for these structurally unprecedented flavoalkaloids that play a key role in the colour range displayed by the Iceland poppy.
Ring-Opening Diarylation of Siloxydifluorocyclopropanes by Ag(I) Catalysis: Stereoselective Construction of 2-Fluoroallylic Scaffold
Song, Xiaoning,Xu, Cong,Du, Dongxu,Zhao, Ziming,Zhu, Dongsheng,Wang, Mang
supporting information, p. 6542 - 6545 (2017/12/26)
A silver-catalyzed, defluorination ring-opening diarylation of siloxy 2,2-difluorocyclopropanes, with two arenes, to directly prepare polysubstituted 2-fluoroallylic compounds, is described. This multicomponent reaction proceeds smoothly in good stereoselectivity, which is due to a chelation-controlled addition of arenes to α-fluorinated ketone intermediate.
145. Synthesis of 3-Methoxy- and 3-(β-D-Glucopyranosyloxy)flavylium Ions. Influence of the Flavylium Substitution Pattern on the Reactivity of Anthocyanins in Aqueous Solution
Dangles, Olivier,Elhajji, Hakima
, p. 1595 - 1610 (2007/10/02)
The synthesis of 3-glycosyloxylated flavylium ions (anthocyanins), in particular of callistephin (4), a natural anthocyanin, is described.The structural transformations in aqueous solution and molecular complexation with chlorogenic acid (7) and caffeine (8) of the synthesized pigments 3 and 4 are investigated and compared to those of the corresponding 3-methoxyflavylium ions 1 and 2 and to those of oenin (5) and malvin (6), two very common natural anthocyanins.The results are discussed in terms of the role played by the glycosyloxy residues in the chemical properties of anthocyanins.Anthocyanin molecular complexation (copigmentation) is quantitatively investigated by UV/VIS spectroscopy and 1H-NMR.In particular, the UV/VIS spectroscopic data are interpreted using a general theoretical treatment, which, e.g., allows to demonstrate the formation of molecular complexes between the colourless forms of an anthocyanin and 8.
