A Highly Stereoselective Synthesis of (3S,4S)-Statine and (3S,4S)-Cyclohexylstatine.
- 1 January 1991
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 39 (9) , 2425-2428
- https://doi.org/10.1248/cpb.39.2425
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.Keywords
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