Enantioselective synthesis of cyclopropane α-amino acids: Synthesis of N-Boc-cis-(2S,3R,4S)-3,4-methanoproline and N-Boc-(2S,3R,4S)-3,4-methanoglutamic acid
✍ Scribed by Isabelle Sagnard; N.André Sasaki; Angèle Chiaroni; Claude Riche; Pierre Potier
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 208 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0040-4039
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Taking advantage of the high functionality of an enantiopure protected syn-2R-amino-l,3,4-triol derivative, easily available on a multigram scale from Disoascorbic acid, several biologically active compounds have been synthesized such as the (2S,3R)-3-amino-2-hydroxydecanoic acid (AHDA), the N-termi
Synthesis of (2S,3R,4S)-3,4-Methanoproline and Analogues by Cyclopropylidene Insertion. -The key steps in the synthesis of the title compounds (IX), (XIII), and (XVI) are stereoselective cyclization of the bromides (V), (X), and (XIV) and oxidation of the bicyclic derivatives (VIII), (XII), and (XV