Oseltamivir: spot the stereochemistry flaw

Single question

Final step in an oseltamivir synthesis: deprotection of an N-Boc amine reveals the free primary amine. The transformation is right. Check the stereochemistry on the cyclohexene ring.

Three contiguous stereocenters on the oseltamivir cyclohexene

(3R,4R,5S) vs (3S,4S,5R) enantiomer activity

Reading absolute stereochemistry on a substituted cyclohexene

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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