Abstract
The first stereoselective total synthesis of new natural amide alkaloids 1-3 have been achieved from commercially available starting materials. Wittig olefination, Sharpless asymmetric dihydroxylation, epoxidation, a trans regioselective opening of 2,3-epoxy alcohol, Horner-Wadsworth-Emmons (HWE) olefination and amide coupling are the key steps. The amide alkaloids 1-3 are evaluated for their anticancer activity against colon (HT-29), breast (MCF-7) and lung (A-549) human cancer cell lines for the first time.
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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Alkaloids / pharmacology
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Amides / chemical synthesis*
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Amides / chemistry
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Amides / pharmacology
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Cell Line, Tumor
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Drug Screening Assays, Antitumor
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Humans
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Piperaceae / chemistry*
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Piperidines / chemical synthesis*
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Piperidines / chemistry
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Piperidines / pharmacology
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Plant Roots / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Amides
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Antineoplastic Agents
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Piperidines