Total Synthesis of the Macrolide Antibiotic 5,6-Dihydrocineromycin B This work was supported by the DFG (SFB 416) and the Fonds der Chemischen Industrie. We thank Prof. Dr. A. Zeeck for supplying data of the title compound, as well as BASF, Degussa-Hüls and Wacker-Chemie for donations of chemicals.

Concepts

Building BlocksBioorganic ChemistryOrganic ChemistryTitle CompoundPharmaceutical ChemistryMedicinal ChemistryMethyl KetoneStereoselective SynthesisBiochemistryTotal SynthesisNatural Product SynthesisPharmacologyBiomolecular EngineeringFacial Selective AllylationNatural SciencesDrug DiscoveryMedicineSynthetic ChemistrySfb 416

Abstract

Three building blocks are coupled convergently in the first total synthesis of the macrolide antibiotic 5,6-tetrahydrocineromycin B (1); the facial selective allylation of a methyl ketone is the key step of the synthesis. TBDMS=tert-butyldimethylsilyl, PMB=p-methoxybenzyl.

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