Synthetic study of polyoxypeptin: stereoselective synthesis of the acyl side-chain segment
โ Scribed by Yasuo Noguchi; Tatsuhiro Yamada; Hiromi Uchiro; Susumu Kobayashi
- Book ID
- 104210834
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 142 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The first synthesis of the acyl side-chain segment of polyoxypeptin, a potent inducer of apoptosis in human pancreatic carcinoma AsPC-1, was accomplished. The key feature of the present synthesis is the stereospecific palladium-catalyzed hydrogenolysis of (Z)-alkenyloxirane to anti-hydroxyalkenoate by an improved method.
๐ SIMILAR VOLUMES
An enantioselective synthesis of the acyl side-chain 3 of polyoxypeptins 1 and 2 was achieved by the Sharpless AE, with subsequent regioselective opening of the epoxyalcohol using a Grignard reagent in the presence of CuI, and an aldol condensation using Seebach's ester. The method reported has the
The lipophilic side chain of the cyclic depsipeptide polyoxypeptin A (1) and B (2), strong apoptosis inducers, has been synthesised as an ester of mixed methyl ketal 18. The key step is an asymmetric anti-aldol reaction of the designed 2-(N-2-methylbenzyl-N-2,4,6-trimethylbenzyl) amino-1-phenylpropy
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
Palladium-catalyzed hydrogenolysis of 4,5-epoxy-2-alkenoates to 5-hydroxy-2-alkenoates was examined, and it was shown that the (Z)-alkenoate with a bulky substituent at C-4 underwent hydrogenolysis with a decrease in the stereospecificity. Mechanistic considerations and steps for improvement of the