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AssigneesVictoria University of Technology, Polychip Pharmaceuticals Pty Ltd
InventorsAndrew John Smallridge, Maurice Arthur Trewhella, Margaret Mary Del Guidice
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This invention relates to yeast-mediated catalysis in organic solvents, and in particular the yeast-mediated condensation between pyruvate and a substituted aromatic aldehyde to yield the corresponding acyloin (hydroxy ketone) compound. The invention provides a method of synthesis of a substituted carbinol compound, comprising the step of subjecting the corresponding substituted aromatic aldehyde to acyloin condensation mediated by a yeast in an organic solvent under non-fermenting conditions. Preferably the yeast is Saccharomyces cerevisiae. In a preferred embodiment, the reaction is that between pyruvate and benzaldehyde to yield phenylacetylcarbinol, the precursor to ephedrine, to yield a product of high enantiomeric purity.
A method of synthesis of a carbinol compound, comprising the step of subjecting the corresponding aromatic aldehyde to an acyloin condensation reaction mediated by a yeast in an organic solvent under non-fermenting conditions, in the presence of an aliphatic alcohol or aliphatic aldehyde, in which the reaction mixture comprises water sufficient to activate the yeast, but not sufficient to form a two phase system.
A method of synthesis of a substituted carbinol compound, comprising the step of subjecting the corresponding substituted aromatic aldehyde to acyloin condensation mediated by a yeast in an organic solvent under non-fermenting conditions, in which the reaction mixture comprises water sufficient to activate the yeast but not sufficient to form a two phase system.
A method of synthesis of a substituted carbinol compound, comprising the step of subjecting the corresponding substituted aromatic aldehyde to acyloin condensation mediated by a yeast in an organic solvent under non-fermenting conditions, in which the reaction is performed at 0-10° C.
Dependencies are inferred from the claim text.