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Revision of the absolute configurations of bethosides B and C and their aglycone

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  • Victoria L Challinor
  • Patricia Y Hayes
  • Paul V Bernhardt
  • William Kitching
  • Reginald P Lehmann
  • James J De Voss

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.

OriginalsprogEngelsk
TidsskriftJournal of Organic Chemistry
Vol/bind76
Udgave nummer17
Sider (fra-til)7275-80
Antal sider6
ISSN0022-3263
DOI
StatusUdgivet - 2 sep. 2011
Eksternt udgivetJa

ID: 169008146