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A novel synthesis of the (2R,3S)- and (2S3R)-3-amino-2-hydroxycarboxylic acid derivatives, the key components of a renin inhibitor and bestatin, from methyl (R)- and (S-mandelate

✍ Scribed by Yuko Kobayashi; Yoshiji Takemoto; Yoshio Ito; Shiro Terashima

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 317 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)89018-8

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✦ Synopsis

The title synthesis could be accomplished by featuring the [2+21-cycloaddition reaction of a chiral imine with benzyloxyketene, alcoholysis of the formed 2-azetidinone derivative, and reductive removal of the mandelate-derived benzylic oxygen by way of a 2-oxazolidone derivative.

Optically active 3-amino-2-hydroxycarboxylic acid derivatives are often involved in medicinally important compounds as their key components. Thus, one of the promising renin inhibitor (1)2)

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