The Synthesis of Polyporic Acid and Atromentin Dimethyl Ether

Abstract

tract was dried over sodium sulfate and evaporated to dryness. The residue was dissolved in hot «-butyl ether. Upon cooling 0.36 g. of dihydrodeguelic acid separated which had the properties recorded for the acid obtained by catalytically reducing deguelic acid. Summary 1.Derric and risic acids have been obtained from deguelic acid by methods analogous to those used in preparing these acids from derivatives of rotenone. This shows that in deguelin as in rotenone, derric acid constitutes one-half of the molecule.2. Reduction of dehydrodeguelin yields dihydrodehydrodeguelin, which is identical with dehydro-j3-dihydrorotenone.3. Upon treatment with alcoholic alkali, dihydrodehydrodeguelin gives dihydrodeguelic acid. This acid is also obtained by catalytically reducing deguelic acid.4. Dihydrodeguelic acid has been found to be identical with dehydrodihydroxy-0-dihydrorotenonic acid described by Haller.5. These facts show that there exist structural relationships common to the entire molecule of both rotenone and deguelin.

p-Terphenyl- and Phenanthraquinone Derivatives: An NMR Study

“…quinones 1 and 2, used as model compounds) and for 9,10phenanthraquinone (9) and retenequinone (10). The chemical shifts were confirmed through correlation spectroscopy and NOE measurements.…”

Elucidation of the Biosynthesis and Degradation of Allantofuranone by Isotopic Labelling and Fermentation of Modified Precursors

“…Hydrolysis with NaOH furnished [D 10 ]polyporic acid (15 a) and 4',4''-difluoropolyporic acid (15 b), respectively. [19] [D 10 ]Polyporic acid (15 a) was fed to a culture of A. lycopodina and the experiment was followed by HPLC/MS. When the production of 1 was detected, mass spectra of the corresponding fraction showed additional ions heavier by 10 Da, giving evidence of enrichment of deuterium in 1.…”

“…288-290 8C; 1 H NMR (400 MHz, [D 6 ]DMSO): d = 7.41 (part of an AA'BB'X system, 4 H; H-2',6',2'',6''), 7.36 ppm (part of an AA'BB'X system, 4 H; H-3',5',3'',5''); 13 [19] Compound 14 a (242 mg, 565 mmol) was suspended in methanol (10 mL), and aq. NaOH (10 %, 10 mL) was added.…”

Side-chain sulfonated random and multiblock poly(ether sulfone)s for PEM applications

“…2,5-Diphenylhydroquinone (DPhHQ) was prepared by a slightly modified procedure described by Shildneck and Adams [27]. A 1L three-necked flask, equipped with a reflux condenser, a thermometer and a 500 mL dropping funnel was charged with a suspension of 150 g (1.125 mol) finely powdered aluminum chloride in 250 mL dry benzene.…”

“…225°C Ref. [27]). 1 H NMR (DMSO-d 6 ): d (ppm): 6.86 (s, 2H); 7.29 (t, 4H); 7.40 (t, 2H); 7.56 (d, 4H); 8.89 (s, 2H; OH).…”