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Acylnitrene route to vicinal amino alcohols. Application to the synthesis of (-)-bestatin and analogues
- Source :
- Journal of Organic Chemistry. April 16, 1999, Vol. 64 Issue 8, p2852, 8 p.
- Publication Year :
- 1999
-
Abstract
- The synthesis of (-)-bestatin and its analogues has been undertaken through a new method. Bestatin and its analogues are naturally occurring small peptides with a nonproteinogenic alpha-hydroxy-beta-amino acid at the N-terminus of the peptide chain. The novel technique uses an intramolecular acylnitrene-mediated aziridination to produce a key bicyclic aziridine in excellent yield and stereoselectivity. The aziridine can be opened by using organometallic reagents to produce a series of substituted oxazolidinones. The latter compounds can be easily transformed to bestatin and its analogues.
- Subjects :
- Organic compounds -- Synthesis
Peptides -- Synthesis
Biological sciences
Chemistry
Subjects
Details
- ISSN :
- 00223263
- Volume :
- 64
- Issue :
- 8
- Database :
- Gale General OneFile
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.54660150