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Tamiflu and the highly potent neuraminidase inhibitor tamiphosphor have been synthesized in 11 steps and greater than 20 % overall yields from an haloarene (1S,2S)-cis-diol. The key transformations include a regio- and stereoselective bromoamidation, and a palladium-catalyzed carbonylation or phosphonylation reaction (see scheme; tamiflu: A=CO2Et, B=NH3+H2PO4−, tamiphosphor: A=PO(ONH4)2, B=NH2).
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Shie et al. (2008) studied this question.
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