Abstract
The first total synthesis of recently isolated diacetylene alcohols oploxyne A, oploxyne B, and their C-10 epimers was accomplished. The structure of natural oploxyne B has been revised. The key steps involved are base-induced double elimination of a carbohydrate-derived β-alkoxy chloride to generate the chiral acetylenic alcohol and Cadiot-Chodkiewicz cross-coupling reaction. The target compounds displayed potent cytotoxicity against neuroblastoma and prostate cancer cell lines.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / pharmacology*
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Antineoplastic Agents / therapeutic use
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Breast Neoplasms / drug therapy
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Breast Neoplasms / pathology
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Catalysis
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Cell Line, Tumor
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Doxorubicin / pharmacology
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Female
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Humans
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Lung Neoplasms / drug therapy
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Lung Neoplasms / pathology
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Male
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Molecular Structure
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Neuroblastoma / drug therapy
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Neuroblastoma / pathology
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Polyynes / chemical synthesis*
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Polyynes / pharmacology*
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Polyynes / therapeutic use
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Prostatic Neoplasms / drug therapy
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Prostatic Neoplasms / pathology
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Stereoisomerism
Substances
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Antineoplastic Agents
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oploxyne B
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Polyynes
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Doxorubicin