The use of norbornene derivatives in the synthesis of conformationally constrained peptides and pseudo-peptides
β Scribed by Iwan G. Jones; Michael North
- Publisher
- Springer Netherlands
- Year
- 1998
- Tongue
- English
- Weight
- 193 KB
- Volume
- 5
- Category
- Article
- ISSN
- 1573-3149
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π SIMILAR VOLUMES
A simple solid-phase method has been developed, in which Pictet-Spengler cyclization is applied on resin for the synthesis of some conformationally constrained tripeptides. This methodology was also used for the synthesis of oxytocin antagonist analogues.
Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5triones, which can be mono-alkylated at N 4, bis-alkylated at N 4 and C 6, or tris-alkylated at N 4, N 1, and C 6 under mild basic conditions; this provides access to i) ct,a-disubstituted cyclic