Organic Letters · 2016 · 24 citations · 34 references
PharmacyChemistryMedicinal ChemistryBiocatalysisNatural Product BiosynthesisSynthetic Medicinal ChemistryMacrocycle SynthesisOrganic SynthesisAsymmetric ReductionsAsymmetric SynthesisEnantioselective SynthesisNatural Product Macrocycle SynthesisNatural Product SynthesisNatural Product Total Synthesis
A de novo asymmetric total synthesis of the macrolide natural product (S)-phoracantholide J has been achieved in 10 steps from the commodity chemicals (1-pentyne, ethyl acrylate, acetaldehyde, and hydrogen). The asymmetry of the route was introduced by a Noyori reduction of a 3-yn-2-one, which makes the route equally amenable to the synthesis of either enantiomer. In addition, this route relies upon an alkyne zipper, a hydroalkynylation, and a macrolactonization to complete the synthesis.
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