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.
A stereoselective synthesis of (3S,4S) statine and related compounds
β Scribed by D Misiti; G Zappia
- Book ID
- 104221885
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 192 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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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.
## Several (3S,4S)-and (3S,4R)-statine derivatives have been prepared by attack of nucleophiles on crystalline, epimeric N-BOC-lactams 7a and 76. The key step in the synthesis of the lactams was the TiC/4-catalyzed coupling reactions of acetals derived from (R)-1,3-butanediol with a//y/trimethy/si
A catalytic deuteration of protected 3,4-dehydro-L-proline using RuCI2(PPh3) 3 followed by RuO~-oxidation gave a 3,4-dideuterated L-pyroglutamic acid derivative which is considered to be a promising precursor for various deuterated amino acids. The present study demonstrates a stereoselective reduct