The Biosynthesis and Synthesis of Shikimic Acid, Chorismic Acid, and Related Compounds

This review considers recent progress in the interpretation of the reaction mechanisms involved in the conversion of glucose into shikimic acid and chorismic acid en route to aromatic compounds. Its main thrust, however, is a detailed survey of the chemical syntheses of shikimic acid and chorismic acid and their derivatives which have been announced in the last decade. 1. The Shikimate Pathway 1.1. Introduction 1.2. The Common Pathway 1.3. The Role of Quinic Acid 1.4. Branch Point Metabolism 2. Syntheses of Shikimic Acid 2.1. Campbell, Sainsbury et al. 2.2. Sunderland et al. 2.3. Rodrigo et al. 2.4. Birch et al. 2.5. Koizumi et al. 2.6. Koreeda et al. 2.7. Koreeda et al. 2.8. Fleet et al. 2.9. Mirza et al. 3. Synthesis of Later Intermediates in the Shikimate Pathway 3.1. Shikimic Acid 3-Phosphate 3.2. 5-Enolpyruvylshikimate-3-phosphate (5-EPS-3-P) 3.3. Chorismic Acid 4. Synthesis of Enzyme Inhibitors 4.1. Synthesis of 5-EPS-3-P Synthase Inhibitors 4.2. Knowles-Anderson