Abstract
The total syntheses of (-)-cylindrocyclophane A (1), a naturally occurring, cytotoxic [7.7]paracyclophane, and its enantiomer have been achieved in an enantiodivergent manner starting from a chiral propargyl alcohol building block using Smith's cross metathesis/ring-closing metathesis protocol as the key step. The biological evaluation of both enantiomers of cylindrocyclophane A (1 and ent-1) and its analogues indicated that the chirality of 1 is irrelevant to its cytotoxicity, which is attributed to the resorcinol motifs embedded in the robust [7.7]paracyclophane framework.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alcohols / chemistry
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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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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Biological Products / pharmacology*
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Cell Proliferation
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HCT116 Cells
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Humans
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Polycyclic Aromatic Hydrocarbons / chemical synthesis*
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Polycyclic Aromatic Hydrocarbons / chemistry
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Polycyclic Aromatic Hydrocarbons / pharmacology*
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Polycyclic Compounds / chemical synthesis*
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Polycyclic Compounds / chemistry
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Polycyclic Compounds / pharmacology*
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Stereoisomerism
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Structure-Activity Relationship
Substances
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(7.7)paracyclophane
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Alcohols
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Antineoplastic Agents
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Biological Products
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Polycyclic Aromatic Hydrocarbons
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Polycyclic Compounds
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cylindrocyclophane A