ABSTRACT
Octandrenolone (1) was prepared in high yield by condensation of 2', 4',6'-trihydroxyacetophenone with 3-chloro-3-methylbut-1-yne in the presence of a catalytic amount of copper(I) iodide. Methylation of 1 afforded O-methyloctandrenolone (2). Oxidation of 2 with m-chloroperoxybenzoic acid followed by hydrolysis gave the racemic trans-(+)-1-(9,10-dihydro-9,10-dihydroxy-5-methoxy-2,2,8, 8-tetramethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-6-yl)ethanone (3), which confirmed the structure of the natural product previously isolated from Melicope erromangensis.
Subject(s)
Acetophenones/chemistry , Acetophenones/chemical synthesis , Chromatography, Thin Layer , Hydrolysis , Indicators and Reagents , Mass Spectrometry , Methylation , Oxidation-Reduction , Plant Roots/chemistry , Plants/chemistry , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
The leaves of Comptonella microcarpa have yielded one alkaloid, dictamnine, and four known polyoxygenated flavonoids, meliternatin, 3,5,8-trimethoxy-6,7-3',4'-dimethylenedioxyflavone, 7-(3-methylbut-2-enyloxy)-3,5,8-trimethoxy-3', 4'-methylenedioxyflavone (3), 7-hydroxy-3,5,8-trimethoxy-3', 4'methylenedioxyflavone. In addition, two new flavonoids were found whose structures were established on the basis of their spectral data as 7-hydroxy-3,5,6,8-tetramethoxy-3',4'-methylenedioxyflavone (1) and 7-(3-methylbut-2-enyloxy)-3,5,6,8-tetramethoxy-3', 4'-methylenedioxyflavone (2).
ABSTRACT
A preliminary screening showed the occurrence of alkaloids only in stem bark of Citrus macroptera Montr. In a first work on this Citrus [only one alkaloid was identified = edulinine]. We report in this paper the isolation of two other alkaloids: (+/-) Ribalinine and Isoplatydesmine and of five aromatic compounds: two derived from cinnamic acid, three identified as syringaldehyde, vanillin and methyl/vanillinate.
Subject(s)
Citrus/chemistry , Alkaloids/isolation & purification , New CaledoniaABSTRACT
A preliminary screening showed the occurrence of alkaloids only in root bark and roots of ESENBECKIA PILOCARPOIDES H. B. K., (Rutaceae). Six alkaloids have been isolated and identified from root bark: one acridone, 1-hydroxy-3-methoxy- N-methyl-acridone; four furoquinolines, maculine, flindersiamine, kokusaginine, kokusagine; the sixth, isomaculine, a furo-4-quinolone, known as a synthetic product, has been isolated for the first time from a natural source.