Synfacts 2020; 16(08): 0992
DOI: 10.1055/s-0040-1707445
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fluorodehydroalanine-Containing Peptides

Hisashi Yamamoto
Tomohiro Hattori
Zhou H, van der Donk WA. * University of Illinois at Urbana-Champaign, USA
Synthesis of 2-Amino-3-fluoroacrylic Acid Containing Peptides.

Org. Lett. 2001;
3: 593-596
Further Information

Publication History

Publication Date:
21 July 2020 (online)



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.