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Synthesis of α‐Hederin, δ‐Hederin, and Related Triterpenoid Saponins
Author(s) -
Plé Karen,
Chwalek Martin,
VoutquenneNazabadioko Laurence
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300723
Subject(s) - chemistry , hederagenin , glycosylation , yield (engineering) , triterpenoid , stereochemistry , arabinose , saponin , organic chemistry , xylose , biochemistry , medicine , materials science , alternative medicine , pathology , fermentation , metallurgy
The synthesis of α‐hederin (3‐ O ‐[α‐ L ‐rhamnopyranosyl‐(1⇄2)‐α‐ L ‐arabinopyranosyl]hederagenin, 1 ), δ‐hederin (3‐ O ‐(α‐ L ‐arabinopyranosyl)hederagenin, 3 ), and three related triterpenoid saponins is described as part of a study of the structure−activity relationships between triterpenoid saponins and hemolytic activity. 4‐Methoxybenzyl α‐ L ‐arabinopyranoside ( 11 ) was synthesized first and then used to prepare the different arabinose acceptors. Glycosylation between the acceptors and 2,3,4‐tri‐ O ‐benzoyl‐α‐ L ‐rhamnopyranosyl trichloroacetimidate ( 20 ) was performed in excellent yield to give the desired disaccharides. Coupling of the trichloroacetimidate derivatives of the disaccharides to allyl‐ or methylhederagenin gave the protected saponosides in high yields. The saponins and their corresponding methyl esters were then obtained in good to moderate yields after deprotection. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)