29799-85-7Relevant academic research and scientific papers
Heterocycles. XXV. Sodium Borohydride Reduction of Flavanonols
Li, Shaoshun,Onda, Masayuki,Kagawa, Hitoshi,Kawase, Hiromi,Iguchi, Mieko,Harigaya, Yoshihiro
, p. 2029 - 2035 (2007/10/02)
Solvent effects on the stereochemistry in the sodium borohydride reduction of (+/-)-flavanonols have been examined.The effects observed for the (+/-)-flavanonols with 5-OMe in 2-propanol, dioxane and methanol are explainable by the differences between the steric interactions inherent in the product-like transition states A and B.It has been also found that 5-OAc peculiarly affects the stereochemistry in the reduction to produce the (+/-)-catechin-type compounds in a one-pot process.The solvent and temperature effects are examined using a model analogous to the above.
SYNTHESIS OF CONDENSED TANNINS. PART 18. STILBENES AS POTENT NUCLEOPHILES IN REGIO- AND STEREO-SPECIFIC CONDENSATIONS: NOVEL GUIBOURTINIDOL-STILBENES FROM GUIBOURTIA COLEOSPERMA
Steynberg, Jan P.,Ferreira, Daneel,Roux, David G.
, p. 1705 - 1712 (2007/10/02)
(E)-3,3',4,5'-Tetrahydroxy- and 3',4,5'-trihydroxy-stilbenes function as strong nucleophiles in regio- and stereo-specific condensations with carbenium ions generated from 2,3-trans- and 2,3-cis-flavan-3,4,4',7-tetraols (leucoguibourtinidins) to generate
BIFLAVANOID PROGUIBOURTINIDIN CARBOXYLIC ACIDS AND THEIR BIFLAVANOID HOMOLOGUES FROM ACACIA LUEDERITZII
Ferreira, Daneel,Preez, I. Cornelius Du,Wijnmaalen, Jacobus C.,Roux, David G.
, p. 2415 - 2422 (2007/10/02)
Key Word Index - Acacia luederitzii; Leguminosae; leucoguibourtinidins; proguibourtinidins; carboxylic acids; 3,4',7-trihydroxyflavanyls; regio-isomerism; diastereoisomers; 6-carboxyl-(+)-catechin; biflavanoids. - - and -proguibourtinidin carboxylic acids (3,7,4'-trihydroxyl functionality) of 2,3-trans-3,4-trans:2,3-cis- and 2,3-trans-3,4-trans:2,3-trans-configuration based on (-)-epicatechin or (+)-catechin as constituent units, and their associated biflavanoid homologues, predominate in the heartwood of Acacia luederitzii.They are accompanied by stereochemical and functional analogues and by their putative flavan-3,4-diol and flavan-3-ol precursors.
