Second generation catalytic asymmetric synthesis of Tamiflu: allylic substitution route.
Catalytic asymmetric synthesis of Tamiflu, an important antiinfluenza drug, was achieved. After the catalytic enantioselective desymmetrization of meso-aziridine 3 with TMSN3, using a Y catalyst (1 mol %) derived from ligand 2, an allylic oxygen function and C1 unit on the C=C double bond were introduced through cyanophosphorylation of enone and allylic substitution with an oxygen nucleophile. This second generation route of Tamiflu is more practical than our previously reported route. [reaction: see text].
Mita
Tsuyoshi
T
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Fukuda
Nobuhisa
N
Roca
Francesc X
FX
Kanai
Motomu
M
Shibasaki
Masakatsu
M
D002384:Catalysis; D008024:Ligands; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D053139:Oseltamivir / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015019:Yttrium / Q000737:chemistry*
D008024:Ligands; D009942:Organometallic Compounds; D053139:Oseltamivir; D015019:Yttrium