Oseltamivir (Tamiflu) Pt. 6
Hayashi, Ishikawa and Suzuki. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200804883.
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It’s back! Not just Tot. Syn., reanimated refreshed after a decent winter break, but Tamiflu too (thanks to all those who flagged this one up for me. In this case, in a (marginally) different guise, as what we’ve got here is Oseltamivir-free base, not the phosphate salt normally isolated. Not an important fact, but the salt formation probably makes quite a difference in-vivo…
However, that doesn’t matter a damn when the synthesis is a sweet at this. To quote Hayashi, this is a ” three one-pot operations” synthesis, so over pretty damn quick; in fact, there’s only one
Norzoanthamine

Kobayashi, Yamashita, Murata, Hikage, Takao, Nakazaki, and Kitahara. ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200804544.
, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200804546.
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When the synthesis is spaced over two papers, you know it’s a biggie; a true beast of a natural product, Norzoanthamine made the gloried pages of Science when it was first completed by Miyashita back in 2004. Bulging with interesting biological activity (the headline being prevention of decrease in bone weight in osteoporotic mice), med-chem work is apparently under way. Coupled with a lack of comments about ’scarcity’ or ‘low isolation yield’, I’d guess that it’s relatively easy to






