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Synthetic study of polyoxypeptin: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline

✍ Scribed by Yasuo Noguchi; Hiromi Uchiro; Tatsuhiro Yamada; Susumu Kobayashi

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 72 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00867-x

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✦ Synopsis

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 the pyrrolidine ring.

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