Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins

被引：40

作者：

Plé, K ^{[1
]}

Chwalek, M ^{[1
]}

Voutquenne-Nazabadioko, L ^{[1
]}

机构：

[1] Univ Reims, CNRS, UMR 6013, F-51687 Reims, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 07期

关键词：

glycosylation; natural products; saponins; total synthesis;

D O I：

10.1002/ejoc.200300723

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The synthesis of a-hederin (3-O-[alpha-L-rhamnopyranosyl(1 --> 2)-alpha-L-arabinopyranosyl]hederagenin, 1), delta-hederin (3-O-(alpha-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 alpha-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-benzOoyl-alpha-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

引用

页码：1588 / 1603

页数：16

共 43 条

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Chemoenzymatic syntheses of naturally occurring β-glucosides [J].