Revision of the Absolute Configurations of Bethosides B and C and Their Aglycone

被引：13

作者：

Challinor, Victoria L. ^{[1
]}

Hayes, Patricia Y. ^{[1
]}

Bernhardt, Paul V. ^{[1
]}

Kitching, William ^{[1
]}

Lehmann, Reginald P. ^{[2
]}

De Voss, James J. ^{[1
]}

机构：

[1] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia

[2] Integria Healthcare, Brisbane, Qld 4113, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 17期

关键词：

STEROIDAL SAPONINS; SAPOGENINS; ANALOGS; PLANTS;

D O I：

10.1021/jo2012797

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute stereochemistry of the steroidal saponins bethosides B and C was previously assigned as (22R,25R) on the basis of work that employed Horeau's method. Our studies of helosides A and B created doubt about both the original assignment and consequently our conclusion that relied upon it. The absolute configurations of bethosides B and C are revised to (22S,25R) following X-ray crystallographic analysis of their aglycone. Synthesis and full spectral characterization of both the 22R and 22S aglycones is reported to facilitate future stereochemical assignments in this series of saponins.

引用

页码：7275 / 7280

页数：6

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