Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate

Guoqing Wei; Justin Chalker; Theodore Cohen

doi:10.1021/jo201341q

Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate

Guoqing Wei, Justin Chalker, Theodore Cohen

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

A highly practical synthesis of enantiopure (-)-α-kainic acid is accomplished in 37% overall yield, using 13 linear steps and a minimum of chromatographic separations via an unprecedentedTMSClpromoted palladium-catalyzed zinc-ene cyclization of an allyl acetate. (Figure presented)

Original language	English
Pages (from-to)	7912-7917
Number of pages	6
Journal	The Journal of Organic Chemistry
Volume	76
Issue number	19
DOIs	https://doi.org/10.1021/jo201341q
Publication status	Published - 7 Oct 2011

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title = "Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate",

abstract = "A highly practical synthesis of enantiopure (-)-α-kainic acid is accomplished in 37% overall yield, using 13 linear steps and a minimum of chromatographic separations via an unprecedentedTMSClpromoted palladium-catalyzed zinc-ene cyclization of an allyl acetate. (Figure presented)",

author = "Guoqing Wei and Justin Chalker and Theodore Cohen",

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AU - Wei, Guoqing

AU - Chalker, Justin

AU - Cohen, Theodore

PY - 2011/10/7

Y1 - 2011/10/7

N2 - A highly practical synthesis of enantiopure (-)-α-kainic acid is accomplished in 37% overall yield, using 13 linear steps and a minimum of chromatographic separations via an unprecedentedTMSClpromoted palladium-catalyzed zinc-ene cyclization of an allyl acetate. (Figure presented)

AB - A highly practical synthesis of enantiopure (-)-α-kainic acid is accomplished in 37% overall yield, using 13 linear steps and a minimum of chromatographic separations via an unprecedentedTMSClpromoted palladium-catalyzed zinc-ene cyclization of an allyl acetate. (Figure presented)

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U2 - 10.1021/jo201341q

DO - 10.1021/jo201341q

M3 - Article

VL - 76

SP - 7912

EP - 7917

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -

Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate

Abstract

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