Enantioselective fluorination mediated by N-fluoroammonium salts of cinchona alkaloids:: First enantioselective synthesis of BMS-204352 (MaxiPost)

被引：101

作者：

Shibata, N

Ishimaru, T

Suzuki, E

Kirk, KL

机构：

[1] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Toyama 9300194, Japan

[2] NIDDK, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 06期

关键词：

D O I：

10.1021/jo026792s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have employed a cinchona alkaloid/Select-fluor-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.

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页码：2494 / 2497

页数：4

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