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Synthesis 1996; 1996(7): 816-818
DOI: 10.1055/s-1996-4315
short paper
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Total Synthesis of the 5-HT3 Receptor Antagonist Palonosetron

Bruce A. Kowalczyk* , Charles A. Dvorak
  • *Chemical Development, Syntex Research, Palo Alto, California 94304, USA, Fax +1(415)3547929
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Publication Date:
31 December 2000 (online)

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A short and efficient synthetic route to the 5-HT3 receptor antagonists 1 and 2 (palonosetron) was developed. The novel adjustment of the oxidation states at the necessary centers of imide 7 was accomplished by hydrogenation, selective sodium borohydride reduction, and dehydration to yield 1. The sodium borohydride reduction of imide 8 was selective for the C-3 carbonyl versus the C-1 carbonyl next to the aromatic ring to give the hydroxy compound 9. It was essential to keep the sodium borohydride reduction free of oxygen, or diols 10a and 10b were formed as significant byproducts.

palonosetron - imide - selective reduction - 5-HT3 receptor antagonist

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