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Synthesis 2000; 2000(8): 1113-1116
DOI: 10.1055/s-2000-6321
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Total Synthesis of RS-42358 and Analogs Using Lateral Lithiation

Bruce A. Kowalczyk*
  • *Chemical Development, Roche Bioscience, 3401 Hillview Avenue, Palo Alto, California 94304, USA; Fax +1 (6 50) 3 54 79 29; E-mail: bruce.kowalczyk@roche.com
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Publikationsdatum:
31. Dezember 2000 (online)

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A short synthesis of the 5-HT3 receptor antagonist RS-42358 was developed based on the condensation of lactone 2 with S3-aminoquinuclidine. The position 2 analogs of RS-42358 were made by condensing various primary amines with lactone 2. The key step in the synthesis of lactone 2 was lateral lithiation of diethyl amide 7 using n-BuLi in THF.

lateral lithiation - 5-HT3 - receptor antagonist - RS-42358