Tang Gang
2001
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Journal
Journal of China Pharmaceutical University
Abstract
AIM\ The purpose is to synthesize 6 fluoro L DOPA (FDOPA). METHODS\ The preparation of FDOPA was based on the nucleophilic displacement of fluorine for nitro group of the commercially available precursor nitroveratraldehyde, reductive iodination, and chiral catalytic phase transfer alkylation, hydrolysis and purification by preparative high pressure liquid chromatography. The enantiomeric purity was determined by HPLC analysis using a chiral mobile phase and a reversed phase C 18 column. RESULTS\ The total yield from nitroveratraldehyde was 33%, the whole reaction time (not include the synthesis time of catalyst) was less than 90 min and the enantiomeric purity was above 95%. CONCLUSION\ A highly regioselective and stereoselective synthesis of FDOPA by chiral catalytic phase transfer alkylation provides an efficient and flexible synthetic route to 6 fluoro L DOPA ( 18 FDOPA) and other aromatic amino acids. HPLC analysis using a chiral mobile phase affords a simple and flexible method for measuring enantiomeric purity of \{\+\{18\} FDOPA\} and other fluoro L amino acids.