An expeditious synthesis of (3S,4S)-statine and (3S,4S)cyclohexylstatine
β Scribed by Yoshiji Takemoto; Teruyo Matsumoto; Yoshio Ito; Shiro Terashima
- Book ID
- 104226485
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 183 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The title synthesis could be accomplished by employing highly stereoselective aldol reaction of Omethyl-0-trimethylsilyl ketene acetal with the (S)-a-amido aldehyde (2) in the presence of titanium (IV) chloride as a key step.
π SIMILAR VOLUMES
Diastcrcomcrically and enantiomerically pure (3S,4S kstatinc (2). the non-prolcinogcnic amino acid of thc protease inhibitor pepstatin (1). has bccn prepared rrom ( R )-2,3-0-isopropylideneglywrddchyde (4) in nine steps and 13% overall yield.
A practical approach for the synthesis of the (2S,3S,4R)-trihydroxyazepane 1d has been reported. Starting from a-D-xylo-pentodialdose, readily available from D-glucose, the sequence involves Wittig olefination and reductive amination as key steps.