Synthesis of Dehydroamino Acids through Stereospecific Elimination
A Stereospecific Elimination to Form Dehydroamino Acids: Synthesis of the Phomopsin Tripeptide Side Chain.
J. Am. Chem. Soc. 1999;
18 November 2019 (online)
Key wordsdehydroamino acids - asymmetric synthesis - cyclic sulfamidites - phomopsin - hydroxyamino acids - elimination
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.