Abstract
We report a facile protocol to obtain 22-substituted furostans and pseudosapogenins in high yields from (25R)- and (25S)-sapogenins. This method involves the treatment of the sapogenin with acetic-trifluoroacetic mixed anhydride and BF(3)·OEt(2) at room temperature, followed by the addition of a nucleophile (H(2)O, MeOH or KSeCN). In the case of 22-hydroxyfurostans, they can be transformed to pseudosapogenins by treatment with p-toluensulfonic acid.
Copyright © 2011 Elsevier Inc. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetic Anhydrides
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Antineoplastic Agents, Phytogenic / analysis
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Benzenesulfonates / chemistry
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Boranes / chemistry
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Chemistry, Pharmaceutical*
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Cyanides / chemistry
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Fluoroacetates
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Magnetic Resonance Spectroscopy
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Methanol / chemistry
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Molecular Structure
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Sapogenins / analysis
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Sapogenins / chemical synthesis*
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Spirostans / analysis
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Spirostans / chemistry*
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Stereoisomerism
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Temperature
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Trifluoroacetic Acid / chemistry
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Water / chemistry
Substances
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Acetic Anhydrides
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Antineoplastic Agents, Phytogenic
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Benzenesulfonates
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Boranes
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Cyanides
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Fluoroacetates
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Sapogenins
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Spirostans
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Water
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boron trifluoride etherate
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trifluoroacetic anhydride
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Trifluoroacetic Acid
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4-toluenesulfonic acid
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Methanol