𝔖 Bobbio Scriptorium
✦   LIBER   ✦

An efficient enantioselective synthesis of the acyl side chain of polyoxypeptins

✍ Scribed by Dong-Guang Qin; Zhu-Jun Yao

Book ID
104252681
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
198 KB
Volume
44
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

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 advantage of a concise route and excellent enantiomeric purity, as well as starting from readily available chemical substrates and the use of inexpensive reagents.

πŸ“œ SIMILAR VOLUMES

Synthetic study of polyoxypeptin: stereo
Synthetic study of polyoxypeptin: stereoselective synthesis of the acyl side-chain segment
✍ Yasuo Noguchi; Tatsuhiro Yamada; Hiromi Uchiro; Susumu Kobayashi πŸ“‚ Article πŸ“… 2000 πŸ› Elsevier Science 🌐 French βš– 142 KB

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

A practical synthesis of the lipophilic
A practical synthesis of the lipophilic side chain of the polyoxypeptins
✍ Miguel Lorca; Michio Kurosu πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 80 KB

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

ChemInform Abstract: A Practical Synthes
ChemInform Abstract: A Practical Synthesis of the Lipophilic Side Chain of the Polyoxypeptins.
✍ Miguel Lorca; Michio Kurosu πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 29 KB πŸ‘ 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a β€œFull Text” option. The original article is trackable v