Synthesis of two natural betulinic acid saponins containing α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranose and their analogues

被引：43

作者：

Gauthier, Charles ^{[1
]}

Legault, Jean ^{[1
]}

Lavoie, Serge ^{[1
]}

Rondeau, Simon ^{[1
]}

Tremblay, Samuel ^{[1
]}

Pichette, Andre ^{[1
]}

机构：

[1] Univ Quebec, Dept Sci Fondamentales, Lab anal & Seperat Essences Vegetales, Chicoutimi, PQ G7H 2B1, Canada

来源：

TETRAHEDRON | 2008年 / 64卷 / 30-31期

关键词：

betulinic acid; lupane-type saponin; alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranose; anticancer;

D O I：

10.1016/j.tet.2008.05.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of naturally occurring betulinic acid saponins bearing an alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside moiety at the C-3 position is described. Betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[ -D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside isolated from Pulsatilla koreana and 28-O-beta-D-glucopyranosyl betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-a-L-arabinopyranoside isolated from Schefflera rotundifolia were easily synthesized for the first time using a stepwise glycosidation approach. The overall syntheses involved eight linear steps starting from allyl betulinate and commercially available L-arabinose, L-rhamnose and D-glucose. The syntheses of betulin and betulinic acid O-glycoside analogues containing an alpha-L-arabinose moiety are also reported. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：7386 / 7399

页数：14

共 72 条

[1] NMR-SPECTROSCOPY IN THE STRUCTURAL ELUCIDATION OF OLIGOSACCHARIDES AND GLYCOSIDES [J].