Synthesis of the proposed core of aeruginosins 205: the new α-amino acid (2S,3aS,6R,7aS)-2-carboxy-6-chlorooctahydroindole
✍ Scribed by Nativitat Valls; Mercè Vallribera; Mercè Font-Bardı́a; Xavier Solans; Josep Bonjoch
- Book ID
- 104359759
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 387 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
The synthesis of enantiomerically pure a-amino acid (2S,3aS,6R,7aS)-2-carboxy-6-chlorooctahydroindole (L-Ccoi) is described. NMR data of L-Ccoi 3 are very different from those reported for the azabicyclic core of aeruginosins 205, indicating that the structure of these aeruginosins needs to be revised.
📜 SIMILAR VOLUMES
The title compound has been prepared as its N-benzyloxycarbonyl urethane in a three-step one-pot reaction in 20-30% yield from the dipeptide derivative Z-Gln-Glu(OH)2. Evidence concerning the configuration and chiral purity of the title compound is given.
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