First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104.
First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104 are reported. A pair of syn diol isomers (NK-104 and its enantiomer) was obtained efficiently by diastereomeric resolution. The synthesis of a pair of anti diol isomers (3-epimer and 5-epimer) was accomplished effectively by the asymmetric aldol reaction followed by anti stereoselective reduction as key steps. Their purity determinations were effected by chiral HPLC analysis.
Suzuki
M
M
Central Research Institute, Nissan Chemical Industries Ltd., Funabashi, Chiba, Japan. suzukimi@nissanchem.co.jp
Yanagawa
Y
Y
Iwasaki
H
H
Kanda
H
H
Yanagihara
K
K
Matsumoto
H
H
Ohara
Y
Y
Yazaki
Y
Y
Sakoda
R
R
D006538:Heptanoic Acids / Q000737:chemistry*; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism
D006538:Heptanoic Acids; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; D011804:Quinolines; C108475:pitavastatin