Helvetica Chimica Acta · 1971 · 39 citations · 1 references
EngineeringNatural SciencesDiversity-oriented SynthesisNew β‐Fragmentation ReactionOrganic ChemistryChemistryHeterocycle ChemistryFeasible SynthesisEnantioselective SynthesisBiomolecular EngineeringExaltolide 1
Abstract Vicinal α‐hydroperoxy‐tetrahydropyranyl ethers annelated to cyclododecane are smoothly converted by homolytic fission in about 75% yield to a mixture of the macrocyclic lactones 3 , 4 , and 5. Based on this observation, an economically feasible synthesis of Exaltolide 1 (>65% yield) has been developed. The mechanism of this new β‐fragmentation reaction is discussed.
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