Abstract
The convergent total synthesis of polycarcin V, a gilvocarcin-type natural product that shows significant cytotoxicity with selectivity for nonsmall-cell lung cancer, breast cancer, and melanoma cells, has been achieved in 13 steps from 7, 8, and 22; the sequence features a stereoselective α-C-glycosylation reaction for the union of protected carbohydrate 7 and naphthol 8. The association constant for the binding of polycarcin V to duplex DNA is similar to that previously reported for gilvocarcin V.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Aminoglycosides
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Cell Line, Tumor
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Coumarins / chemical synthesis*
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Coumarins / chemistry*
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DNA / chemistry*
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Glycosides / chemical synthesis*
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Glycosides / chemistry*
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Glycosylation
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Humans
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Molecular Structure
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Naphthols / chemistry*
Substances
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Aminoglycosides
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Anti-Bacterial Agents
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Antineoplastic Agents
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Biological Products
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Coumarins
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Glycosides
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Naphthols
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polycarcin V
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gilvocarcin V
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DNA