Tetrahedron p. 13881 - 13894 (1996)
Update date:2022-07-30
Topics:
Iwasawa, Yoshikazu
Shibata, Jun
Nonoshita, Katsumasa
Arai, Sachie
Masaki, Hitoshi
Tomimoto, Koji
A novel class of squalene synthase inhibitors (J-104,118 and J-104,123) were synthesized efficiently. An amine intermediate 1 was synthesized using two distinct methods. First, the racemic amine 1 was synthesized diastereoselectively using a key reaction consisting of the stereo-controlled reduction of the ketone 7 by L-Selectride. Second, the optically active amine 1 was synthesized efficiently and enantioselectively using Sharpless dihydroxylation as a key reaction. A stereo-controlled method for synthesizing J-104,123 was developed starting from a commercially available methyl (R)-3-hydroxybutyrate.
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