A Stereospecific Conversion of (−)-Methyl Tri-O-benzoylquinate to the Corresponding (−)-Methyl Shikimate

✍ Scribed by Dr. J. Cleophax; D. Mercier; Dr. S. D. Géro

• Book ID: 101549150
• Publisher: John Wiley and Sons
• Year: 1971
• Tongue: English
• Weight: 228 KB
• Volume: 10
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197106522

✦ Synopsis

of the steps (5e)+(4e)+(6e). However (4a), which differs only slightly from (4e), could be recovered in 66% yield after 24-h treatment with aqueous ammonium chloride. Hydrolysis of ( 4 a ) and (4 b) requires drastic conditions (KOH in dioxane/water, 24 h, 100°C) and affords 70% of (7ajr9] and (7b), respectively. The independently prepared ( 6 a ) could not be detected by tlc. This regiospecificity of ring opening (path B) parallels the course of the Favorskii rearrangement[', ' I. The described variation of this reaction opens novel synthetic possibilities.