Total synthesis of the unusual cyclosporine amino acid MeBMT
β Scribed by Roger D Tung; Daniel H Rich
- Book ID
- 108382711
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 269 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
The syntheses of four olefinic analogs of Cyclosporin A at amino acid one (MeBMT), a residue critical for the Cyclophilin binding domain, are reported. The synthetic process is a rapid, general, semi-synthetic sequence involving oxidative degradation of the olefinic sidechain followed by a Wittig ol
## Abstract For Abstract see ChemInform Abstract in Full Text.
A syn-(2R)-amino-l,3,4-butanetriol derivative, readily available from Disoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chir