Efficient Activation of Zinc: Application of the Blaise Reaction to an Expedient Synthesis of a Statin Intermediate

Hyunik Shin; Bo Seung Choi; Ki Kon Lee; Hyeong-wook Choi; Jay Hyok Chang; Kyu Woong Lee; Do Hyun Nam; No-Soo Kim

doi:10.1055/s-2004-831197

PAPER

Efficient Activation of Zinc: Application of the Blaise Reaction to an Expedient Synthesis of a Statin Intermediate

Hyunik Shin*^a, Bo Seung Choi^a, Ki Kon Lee^a, Hyeong-wook Choi^a, Jay Hyok Chang^a, Kyu Woong Lee^a, Do Hyun Nam^a, No-Soo Kim*^b
^a Chemical Development Division, LG Life Sciences, Ltd./R&D, 104-1, Moonji-dong, Yusong-gu, Daejon 305-380, Korea
^b Faculty of Life Science Engineering, Youngdong University, San 12-1 Sulkye-ri Yeongdong-eup Yeongdong-gun Chungbuk, Korea
Fax: +82(42)8665754; e-Mail: hisin@lgls.co.kr;

Abstract

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Abstract

Efficient and practical in situ zinc activation was accomplished by treatment with catalytic amount of an organic acid. The protocol was applied successfully to the Blaise reaction of various nitriles. Noteworthy is the excellent Blaise transformation of (S)-4-chloro-3-trimethylsilyloxybutyronitrile (2b) into tert-butyl (S)-6-chloro-5-hydroxy-3-oxohexanoate (1), a key intermediate for the preparation of HMG-CoA reductase inhibitors (statins).

Key words

in situ zinc activation - Blaise reaction - statin intermediate

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References

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