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Creators/Authors contains: "Broussy, Sylvain"

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  1. ; ; ; (, The Journal of Organic Chemistry)
    null (Ed.)
    Hybrid synthetic organic/biocatalytic entry into the Tamiflu core, utilizing KRED-reporting enzymes from ISES (In Situ Enzymatic Screening) to set the stereochemistry. The key alpha,beta-unsaturated ketone substrate is obtained by Birch reduction from m-anisic acid. The Birch reduction is conducted either by traditional dissolving metal conditions, or by the electrosynthetic variant recently reported by P. Baran and co-workers. The enzymatic step is novel in that one stereocenter is 'dialed in' almost perfect (i.e. nearly perfect facial selectivity is shown ) whereas the pre-existing stereocenter is 'dialed out' almost perfectly, as desired, to give complete throughput. Following enzymatic reduction, the C-O stereocenter that was set enzymatically is parlayed into a the C-N stereocenter required for Tamiflu. This paper has been selected for the cover of JOC 
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