Abstract
A highly efficient regio- and stereoselective total synthesis of (±)-grandifloracin via a tandem dearomative epoxidation/spontaneous Diels-Alder cyclodimerization from salicylic acid in only four steps is reported. The synthetic route allows for late-stage diversification of the core structure to give ready access to analogues of this promising agent against pancreatic cancer.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Acylation
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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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Bridged-Ring Compounds / chemical synthesis*
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Bridged-Ring Compounds / pharmacology
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Bridged-Ring Compounds / therapeutic use
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Cycloaddition Reaction
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Dimerization
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Molecular Structure
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Pancreatic Neoplasms / drug therapy*
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Salicylic Acid / chemistry*
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Stereoisomerism
Substances
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Antineoplastic Agents
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Bridged-Ring Compounds
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grandifloracin
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Salicylic Acid