The first synthesis of (2S,3R)-3-hydroxy-3-methylproline, which is a novel amino acid of polyoxypeptin, a potent inducer of apoptosis in human pancreatic carcinoma AsPC-1, was accomplished. The key feature of the synthesis is the palladium-catalyzed intramolecular N-allylation of alkenyloxirane to t
Synthetic studies on polyoxypeptins: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline using SmI2-mediated cyclization
β Scribed by Kazuishi Makino; Ai Kondoh; Yasumasa Hamada
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 75 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline (3), a component of polyoxypeptins, has been achieved by use of SmI 2 -mediated diastereoselective cyclization reaction as a key step.
π SIMILAR VOLUMES
## Abstract For Abstract see ChemInform Abstract in Full Text.
Reduction of ethyl 2-allyl-3-oxobutanoate by an enzyme fraction obtained from bakers' yeast results in the formation of ethyl (a,%)-sun-2-allyl-3-hydroxybutanoate in an excellent stereoselectivity. ## Diastereomerically as well as enantiomerically pure 2-allyl-3-hydroxy-