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How Stable Are Epoxides? A Novel Synthesis of Epothilone B
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2000
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Medicinal ChemistrySynthetic StepsEngineeringEnantioselective SynthesisOxirane FunctionMedicineEpothilone BRemarkable StabilityOrganic ChemistryStereoselective SynthesisPharmacologyPharmaceutical ChemistrySynthetic ChemistryBiomolecular EngineeringDrug DiscoveryNatural Product Synthesis
Remarkable stability of the oxirane function is displayed over a number of synthetic operations in a novel synthesis of the antitumor compound epothilone B (see scheme). The cis-epoxide, generated very early by dihydroxylation of an (E)-olefin, was resistant to more than ten synthetic steps under a wide variety of reaction conditions. TBS=tert-butyldimethylsilyl.