A Highly Stereoselective Synthesis of (3A,4iS)-Statine and (SS^AJ-Cyclohexylstatine^

Yoshiji Takemoto, Teruyo Matsumoto, Yoshio Ito, Shiro Terashima

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The title compounds, which are synthetic intermediates of renin inhibitors, could be prepared from (*S)-leucine and (iS)-phenylalanine, respectively, by employing highly stereoselective aldol reactions of 0-methyl-O-trimethylsilyl ketene acetal with an (S)-a-amino aldehyde in the presence of titanium(IV) chloride as a key step. Maximum diaster-eoselectivity of the aldol reaction was found to be more than 95:5.

Original languageEnglish
Pages (from-to)2425-2428
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume39
Issue number9
DOIs
Publication statusPublished - Jan 1 1991

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Acetals
Titanium
Phenylalanine
Renin
Aldehydes
Leucine
Chlorides
statine
3-hydroxybutanal
ketene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

A Highly Stereoselective Synthesis of (3A,4iS)-Statine and (SS^AJ-Cyclohexylstatine^. / Takemoto, Yoshiji; Matsumoto, Teruyo; Ito, Yoshio; Terashima, Shiro.

In: Chemical and Pharmaceutical Bulletin, Vol. 39, No. 9, 01.01.1991, p. 2425-2428.

Research output: Contribution to journalArticle

Takemoto, Yoshiji ; Matsumoto, Teruyo ; Ito, Yoshio ; Terashima, Shiro. / A Highly Stereoselective Synthesis of (3A,4iS)-Statine and (SS^AJ-Cyclohexylstatine^. In: Chemical and Pharmaceutical Bulletin. 1991 ; Vol. 39, No. 9. pp. 2425-2428.
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