A Highly Stereoselective Synthesis of (3S, 4S)-Statine and (3S, 4S)-Cyclohexylstatine

Yoshiji TAKEMOTO; Teruyo MATSUMOTO; Yoshio ITO; Shiro TERASHIMA

doi:10.1248/cpb.39.2425

Yoshiji TAKEMOTO, Teruyo MATSUMOTO, Yoshio ITO, Shiro TERASHIMA

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Keywords: renin inhibitor, (3S, 4S)-statine, (3S, 4S)-cyclohexylstatine, aldol reaction, ketene acetal, (S)-α-amide aldehyde, Lewis acid, titanium(IV) chloride, chelation-control

JOURNAL FREE ACCESS

1991 Volume 39 Issue 9 Pages 2425-2428

DOI https://doi.org/10.1248/cpb.39.2425

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Abstract

The title compounds, which are synthetic intermediates of renin inhibitors, could be prepared from (S)-leucine and (S)-phenylalanine, respectively, by employing highly stereoselective aldol reactions of O-methyl-O-trimethylsilyl ketene acetal with an (S)-α-amino aldehyde in the presence of titanium(IV) chloride as a key step. Maximum diastereoselectivity of the aldol reaction was found to be more than 95 : 5.

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