Enantioselective Fluorination Mediated by <i>N</i>-Fluoroammonium Salts of Cinchona Alkaloids: First Enantioselective Synthesis of BMS-204352 (MaxiPost)
The Journal of Organic ChemistryPublished 13 February 2003
Norio Shibata, Takehisa Ishimaru, Emiko Suzuki, Kenneth L. Kirk
Citations101
SJR quartileQ2
SJR score0.74
SNIP0.86
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TL;DR
A cinchona alkaloid/Selectfluor-mediated enantioselective fluorination of the oxindole 2 is employed to achieve the first enantioslective synthesis of BMS-204352 (MaxiPost, S-1), an effective opener of maxi-K channels.
Abstract
We have employed a cinchona alkaloid/Selectfluor-mediated enantioselective fluorination of the oxindole 2 to achieve the first enantioslective synthesis of BMS-204352 (MaxiPost, S-1), an effective opener of maxi-K channels. Fluorination occurred to produce S-1 with 84% ee using the bis-cinchona alkaloid (DHQ)(2)AQN. Recrystallization produced enantiomerically pure (>99% ee) product. Quinidine-mediated fluorination of 2 gave the (R)-antipode of 1 with 68% ee.
Keywords
ChemistryBiochemistry, Genetics and Molecular BiologyPharmacology, Toxicology and Pharmaceutics
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