Abstract
(+)-Allomatrine (1) has been synthesized using an imino-aldol reaction and N-acyliminium cyclization as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enabled the staged formation of three C-C bonds, a C-N bond, and the four stereogenic centers within the target.
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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Cyclization
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Matrines
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Molecular Conformation
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Molecular Structure
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Quinolizines / chemical synthesis*
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Quinolizines / chemistry
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Sophora / chemistry
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Stereoisomerism
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Trimethylsilyl Compounds / chemistry
Substances
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Alkaloids
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Quinolizines
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Trimethylsilyl Compounds
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allomatrine
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Matrines