First systematic chiral syntheses of two pairs of enantiomers with 3, 5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104

…, H Kanda, K Yanagihara, H Matsumoto, Y Ohara…

Index: Suzuki, Mikio; Yanagawa, Yoshinobu; Iwasaki, Hiroshi; Kanda, Hiroyasu; Yanagihara, Kazufumi; Matsumoto, Hiroo; Ohara, Yoshio; Yazaki, Yukari; Sakoda, Ryozo Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 20 p. 2977 - 2982

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Citation Number: 27

Abstract

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 ...