SYNTHESIS OF ALPHA-DEHYDROAMINO ACID

Synthetic studies on α-dehydroamino acid (DHA) derivatives, which are very important constituents in an increasing number of antibiotic and phytotoxic peptides, were reviewed according to the following articles: 1. Introduction. 2. Synthesis of DHA. 2. 1. From unsaturated azlactones. 2. 2. Elimination of β-substituents. 2. 3. Reduction of α-nitro-α-alkenoic esters. 2. 4. Condensation of α-keto esters with phosphinimines. 2. 5. Condensation of α-keto acids with nitriles or amides. 2. 6. Elimination of N- or α-substituents. 2. 7. Reduction of α-azido-α-alkenoic esters 35. 2. 8. Reduction of 35 with phosphins or phosphites. 3. Synthesis of β-substituted-DHA. 3. 1. β-Halo-DHA. 3. 2.β-Nitro- and azido-DHA. 3. 3.β-Amino-DHA. © 1979, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.