Synfacts 2019; 15(12): 1448
DOI: 10.1055/s-0039-1691277
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Dehydroamino Acids through Stereospecific Elimination

Hisashi Yamamoto
Manthena Chaithanya
Stohlmeyer MM, Tanaka H, Wandless TJ. * Stanford University, USA
A Stereospecific Elimination to Form Dehydroamino Acids: Synthesis of the Phomopsin Tripeptide Side Chain.

J. Am. Chem. Soc. 1999;
121: 6100-6101
Further Information

Publication History

Publication Date:
18 November 2019 (online)



Dehydroamino acids are present in various biologically active natural products. The authors have developed an efficient and stereoselective method for the synthesis of tri- or tetrasubstituted α,β-dehydroamino acids from readily available β-hydroxyamino acids.



Cyclic sulfamidites, derived from readily available β-hydroxyamino acids, are efficient substrates for the stereoselective synthesis of α,β-dehydroamino acids. The developed method was used in a synthesis of the tripeptide side chain of phomopsin A.