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Synthesis 2010(3): 403-406
DOI: 10.1055/s-0029-1217122
DOI: 10.1055/s-0029-1217122
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Facile Chiral Pool Synthesis of (S)-6-Nitroindoline-2-carboxylic Acid from l-Phenylalanine
Further Information
Received
28 August 2009
Publication Date:
13 November 2009 (online)
Publication History
Publication Date:
13 November 2009 (online)
Abstract
(S)-6-Nitroindoline-2-carboxylic acid, a substructure occurring in numerous biologically active natural products, was synthesized with moderate yield (53%) and high enantiomeric excess (>99.5%) starting from the nitration of l-phenylalanine, which is a commercially available chiral pool compound, followed by successively bromination and intramolecular cyclization. The route was carried out in gram quantities and it is suitable for industrial application due to its convenient reaction conditions and low cost.
Key words
chiral pool synthesis - (S)-6-nitroindoline-2-carboxylic acid - l-phenylalanine - 2-bromo-4-nitro-l-phenylalanine - intramolecular cyclization
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