A practical and azide-free synthetic approach to oseltamivir from diethyl D-tartrate.

A practical synthesis of zanamivir phosphonate congeners with potent anti-influenza activity.

Two phosphonate compounds 1a (4-amino-1-phosphono-DANA) and 1b (phosphono-zanamivir) are synthesized and shown more potent than zanamivir against the neuraminidases of avian and human influenza viruses, including the oseltamivir-resistant strains. For the first time, the practical synthesis of these phosphonate compounds is realized by conversion of sialic acid to peracetylated phosphono-DANA d...

Synthesis of tamiflu and its phosphonate congeners possessing potent anti-influenza activity.

Influenza remains a major health problem for humans and animals.1 At present, four drugs are approved for influenza prophylaxis and treatment:2 amantadine and rimantadine act as the M2 ion channel blockers, whereas Tamiflu (the phosphate salt of oseltamivir ethyl ester) and Relenza (zanamivir) inhibit the activity of neuraminidase (NA). The NA inhibitors (NAIs) are designed to have (oxa)cyclohe...

Diphenyl Phosphorazidate (DPPA) − More Than Three Decades Later

More than thirty years have already elapsed since we introduced diphenyl phosphorazidate (diphenylphosphoryl azide, DPPA, (PhO)2P(O)N3) as a reagent for organic synthesis in 1972 (Figure 1). During these years, DPPA has been found to be effective for a variety of organic reactions as a versatile synthetic reagent. It is not too much to say that DPPA has secured an established position as a reag...

Mutagenic interactions in combined treatments of ethylmethane sulphonate,diethyl sulohate and sodium azide on barley

A short enantioselective pathway for the synthesis of the anti-influenza neuramidase inhibitor oseltamivir from 1,3-butadiene and acrylic acid.

A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensive and abundant starting materials; (2) complete enantio-, regio-, and diastereocontrol; (3) avoidance of explosive, azide-type intermediates; ...