Abstract
Synthesis of (22 R)- and (22 S)-27-norspirosolane alkaloids from tigogenin, epismilagenin, and smilagenin is described. The alkaloids were prepared from readily available dinorcholanic lactones via their reaction with 4-chlorobutyllithium followed by substitution of chloride with azide and reductive N-cyclization under the Staudinger conditions.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Crystallography, X-Ray
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Lactones / chemical synthesis*
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Lactones / chemistry
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Magnetic Resonance Spectroscopy
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Spirostans / chemical synthesis*
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Spirostans / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Lactones
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Spirostans
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sarsasapogenin