Zur Kenntnis der Sesquiterpene und Azulene. 113. Mitteilung. Azulenaldehyde und Azulenketone: Die Struktur des Lactaroviolins

Abstract

Zusammenf assung. Bei der Bildung von Phenyl-naphtyl-carbazol-carbonsB;ure aus 2 , s -Oxynaphtoesaure und markiertem Phenylhydrazin 15NHz.NHCsH5 1B;uft ein gemischter Reaktionsmechanismus ab, bei dem der Carbazolring zu 1 2 yo mit dem markierten Stickstoff der Aminogruppe und zu 88 Yo mit unmarkiertem Stickstoff aufgebaut wird.

Total Synthesis of Azulene Derivative, a Blue Pigment Isolated from Lactarius indigo, and Colorant Application of Its Aqueous Dispersion

“…The azulene ring can be constructed via the Ziegler–Hafner method followed by carbometalation. Azulene derivative 1 can be obtained from lactaroviolin 2 , a natural red pigment discovered in Lactarius deliciosus in 1954, via reduction and esterification with stearic acid. The formyl group of 2 can be assembled from 3 using the Vilsmeier–Haack reaction.…”

“…Other Lactarius species and Artemisia arborescens have natural pigments with azulene skeletons similar to those in the synthesized natural pigments 1 and 2. 10,[14][15][16][17]34 Therefore, our synthetic route could be used for the total synthesis of similar derivatives containing a core azulene skeleton. Furthermore, we demonstrated the ability of producing the nanoparticles dispersion of the synthesized 1, prepared using the reprecipitation method, to color aqueous dispersions.…”

“…Moreover, azulene derivatives with an isopropenyl group at the C-5 or C-7 position have rarely been synthesized. Therefore, a robust synthesis of this azulene derivative would not only allow the exploration of the basic properties of the pigments isolated from Lactarius species − but also promote the development of azulene chemistry. In this study, we developed the first total synthesis of azulene derivative 1 .…”

Lactariolines A and B: new guaiane sesquiterpenes with a modulatory effect on interferon-γ production from the fruiting bodies of Lactarius hatsudake

“…7 During the investigation of novel bioactive metabolites from L. hatsudake, we identified two new guaiane sesquiterpenes, lactariolines A (1) and B (2) (Figure 1), along with four known related compounds, 4-methyl-7-isopropylazulene-1-carboxylic acid (3), 1-formyl-4-methyl-7-isopropyl azulene (4), lactaroviolin (5) and 1-formyl-4-methyl-7-(1-hydroxy-1-methylethyl) azulene (6). 8,9 In this study, we describe the isolation, structure elucidation and biological activity of two new compounds.…”