88079-93-0Relevant academic research and scientific papers
SYNTHESIS AND CHARACTERIZATION OF PROCYANIDIN DIMERS AS THEIR PERACETATES AND OCTAMETHYL ETHER DIACETATES
Kolodziej, Herbert
, p. 1209 - 1216 (1986)
Key Word Index - Biomimetic synthesis; procyanidins B1-B8; 3,4-cis-biflavanoid; all--bi--(+)-catechin; 1H NMR parameters. Condensation of (2R,3S,4R or S)-leucocyanidin or the 5,7,3',4'-tetramethyl ether of (2R,3R,4S)-leucocyanidin with flavan-3-ols yielded dimeric flavanoids which were converted to their octamethyl ether diacetates, or the deca-acetates for the 2,3-trans-procyanidin series.Comparison is made of the 1H NMR spectra of the deca-acetate and octamethyl ether diacetate derivatives which lead to useful diagnostic shift parameters characteristic of their structures.Condensation afforded a novel biflavanoid with a 3,4-cis-configuration and a triflavanoid of 'mixed' stereochemistry.
Synthetic studies of proanthocyanidins. Part 2: Stereoselective gram-scale synthesis of procyanidin-B3
Saito, Akiko,Nakajima, Noriyuki,Tanaka, Akira,Ubukata, Makoto
, p. 7829 - 7837 (2007/10/03)
A stereoselective synthesis of procyanidin-B3, a condensed catechin dimer, is described. Condensation of benzylated catechin with various 4-O-alkylated flavan-3,4-diol derivatives as an electrophile in the presence of a Lewis acid led to protected procyanidin-B3 and its diastereomer. In particular, the reaction using (2R,3S,4S)-3-acetoxy-5,7,3′,4′-tetrabenzyloxy-4-(2″- ethoxyethoxy)flavan as an electrophile in the presence of TMSOTf at -78°C afforded octa-O-benzylated procyanidin-B3 with high levels of stereoselectivity and in excellent isolation yields. Furthermore, we succeeded in a stereoselective gram-scale synthesis of protected procyanidin-B3.
Synthesis and Conformation of Procyanidin Diastereoisomers
Foo, Lai Yeap,Porter, Lawrence J.
, p. 1535 - 1543 (2007/10/02)
The four theoretically possible diastereoisomeric 4->8 linked procyanidin dimers with two 2,3-cis-flavanoid units, epicatechin-(4β->8)-epicatechin (6), epicatechin-(4β->8)-ent-epicatechin (8), ent-epicatechin-(4α->8)-epicatechin (7), and ent-epicatechin-(4α->8)-ent-epicatechin (2), have been synthesized together with the 2,3-trans diastereoisomers catechin-(4α->8)-catechin (14) and catechin-(4α->8)-ent-catechin (15).The preferred rotamer conformations of the deca-acetate derivatives of (6), (8), (14), and (15) in chloroform were deduced from their 13C n.m.r. and high-field 1H n.m.r. spectra.The 1H n.m.r. spectra of the preferred conformers of the pairs of acetate derivatives of (6) and (15), and (8) and (14), were qualitatively similar as the relative configuration about the interflavanoid bond of one pair has a meso-relationship to the other.
