Bulletin of the Chemical Society of Japan p. 1093 - 1100 (1999)
Update date:2022-08-28
Topics:
Kajiro, Hiroshi
Mitamura, Shuichi
Mori, Atsunori
Hiyama, Tamejiro
A synthesis of (1S,2R)-1-amino-2-indanol (1), a key component of an HIV protease inhibitor, was accomplished through (R)-2-hydroxy-1-indanone ((R)- 3), which was prepared by an intramolecular Friedel-Crafts acylation of (R)2- acetoxy-3-phenylpropanoic acid readily available from D-(R)-phenylalanine. Alternatively, (R)-3 was obtained by an enzymatic resolution of (±)-2- acetoxy-1-indanone. Ketone (R)-3 was convened into 1 through an oxime formation and diastereoselective hydrogenation.
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