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Synthesis of Fluorodehydroalanine-Containing Peptides
Synthesis of 2-Amino-3-fluoroacrylic Acid Containing Peptides.
Org. Lett. 2001;
21 July 2020 (online)
Key wordsdehydroalanine - aminofluoroacrylates - fluoro-Pummerer rearrangement - fluorodehydroalanine
Dehydroalanine moieties occur abundantly as scaffolds in natural products. Also, fluorine-substituted compounds have received increasing attention due to their small steric bulk and their lipophilicity. The authors developed a strategy for the synthesis of fluorine-substituted dehydroalanines.
(E)- And (Z)-fluorodehydroalanines were synthesized from N-protected serines through a fluoro-Pummerer rearrangement. Moreover, this methodology can be applied in dipeptide synthesis.