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Conjugate Addition of a Cyano-Gilman Cuprate to an Acrylic Acid: Homologation of Artemisinic Acid and Subsequent Conversion to 16-Butylartemisinin
10
Citations
23
References
1998
Year
Bioorganic ChemistryEngineeringArtemisinic Acid 2Organic ChemistryPharmaceutical ChemistryCyano-gilman CuprateBiosynthesisAcrylic AcidNatural Product BiosynthesisPhytopharmacologyBiochemistryArtemisinic AcidBioconjugationPharmacologyNatural Product SynthesisBiomolecular EngineeringAcrylic Acid MoietySitu ProtectionNatural SciencesPhytochemistrySynthetic ChemistryDrug Discovery
Abstract Conjugate addition to the acrylic acid moiety of artemisinic acid 2 was made possible by in situ protection as a silyl ester, treatment with a cyano-Gilman cuprate [Bu2CuLi·LiCN] to facilitate 1,4-addition, and deprotective workup affording the homologated carboxylic acid 9. Photoxygenation and acid treatment of 9 then led to the facile preparation of potent antimalarial 9-modified analogs of artemisinin.
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