47335-95-5Relevant academic research and scientific papers
SYNTHESIS OF ROCAGLAMIDE NATURAL PRODUCTS VIA PHOTOCHEMICAL GENERATION OF OXIDOPYRYLIUM SPECIES
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Sheet 13, (2008/06/13)
The present invention provides new strategies for the synthesis of compounds of the rocaglamide family and related natural products. In particular, the new biomimetic synthetic approach involves photochemical generation of an oxidopyrylium species from a
Stereoselective synthesis of flavonoids. Part 4. Trans- and cis-dihydroflavonols
Van Rensburg, Hendrik,Van Heerden, Pieter S.,Bezuidenhoudt, Barend C.B.,Ferreira, Daneel
, p. 14141 - 14152 (2007/10/03)
Epoxidation of a series of poly-oxygenated chalcones with H2O2 in the presence of poly-α-aminoacids yielded chiral aromatic oxygenated oxiranes in moderate to high optical yields. Lewis acid-catalysed phenylmethanethiol ringopening o
The first enantioselective synthesis of trans- and cis-dihydroflavonols
Van Rensburg, Hendrik,Van Heerden, Pieter S.,Bezuidenhoudt, Barend C. B.,Ferreira, Daneel
, p. 2747 - 2748 (2007/10/03)
Epoxidation of a series of polyoxygenated chalcones with H2O2 in the presence of poly(α-amino acid) catalysts, followed by Lewis acid-catalysed phenylmethanethiol ring-opening and cyclization, afforded trans- and cis-dihydroflavonols
Heterocycles. XXII. Stereoselective Synthesis of (+)-Aromadendrin Trimethyl Ether and Its Enantiomer, and Their Reduction
Takahashi, Hiroshi,Li, Shaoshun,Harigaya, Yoshihiro,Onda, Masayuki
, p. 1877 - 1881 (2007/10/02)
Two enantiomeric chalcone epoxides 2a and 2b are synthesized under phase-transfer conditions using 1-benzylquinidinium chloride and 1-benzylquininium chloride as catalysts, respectively.Stereoselective cyclisation of 2a and 2b, followed by methylation and
HETEROCYCLES. XVIII. SYNTHESIS OF THE RACEMATES OF NATURALLY OCCURRING FLAVONOIDS
Takahashi, Hiroshi,Kubota, Yumiko,Igushi, Mieko,Fang, Lin,Onda, Masayuki
, p. 369 - 377 (2007/10/02)
Racemic aromadendrin and fustin have been stereoselectively synthesized.Reduction of the O-substituted derivatives of these flavanonols provides the corresponding derivatives of gleditsin, leucopelargonidin and mollisacacidin (leucofisetinidin).
AURAPIN, A NEW DIHYDROFLAVONOL GLYCOSIDE AND OTHER FLAVONOIDS FROM ACINOS ALPINUS
Venturella, Pietro,Bellino, Aurora,Marino, Maria Luisa,Sorrentino, Marco
, p. 1979 - 1982 (2007/10/02)
A new dihydroflavonol glycoside has been isolated from Acinos alpinus and identified as 3-O-rhamnosyl-5-hydroxy-7,4'-dimethoxyflavanone on the basis of chemical and spectroscopic evidence.Three known flavonoids (naringenin, taxifolin and neoponcirin) were additionally isolated from same source.
Some Novel Photochemical and Related Aryl Couplings and Migrations in Flavonoid Synthesis
Westhuizen, Jan H. van der,Ferreira, Daneel,Roux, David G.
, p. 2856 - 2865 (2007/10/02)
2'-Methoxymethoxy-4,4',6'-trimethoxychalcone epoxide couples at the β-position with 3,5-dimethoxyphenol under photolytic conditions to form isomeric 1,3,3-triaryl-2-hydroxypropiophenones.These propiophenones are subject to photo-induced α-ketol rearrangements yielding isomeric 1-hydroxypropan-2-ones.Together these serve as useful synthetic intermediates for 4-arylflavan-3-ones and novel 2-hydroxy-2-arylbenzylbenzofuran-3(2H)-ones and 4-aryl-3-hydroxy-3,4-cis-dihydrocoumarins.The same epoxide reacts ionically under ambient conditions with 2,4,6-trihydroxybenzoic acid to afford a 3-O-benzoylpropiophenone intermediate, which provides novel access to isoflavones in high overall yield.Analogous coupling of phloroglucinol to epoxycinnamates gives diastereoisomeric 3,3-diaryl-2-hydroxypropionates which serve as precursors for 3,4-trans- and 3,4-cis-4-aryl-3-hydroxydihydrocoumarins and thence for 3-aryl- and 3-hydroxycoumarins.
