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Issue 31, 2017
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Total synthesis of (−)-kainic acid and (+)-allo-kainic acid through SmI2-mediated intramolecular coupling between allyl chloride and an α,β-unsaturated ester

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Abstract

A 3,4-disubstituted pyrrolidine ring was effectively cyclized through SmI2-mediated reductive coupling between allyl chloride and an α,β-unsaturated ester, although little has been reported about SmI2-promoted C–C bond formation of an allyl chloride with an α,β-unsaturated ester. Selection of either the 3,4-cis- or 3,4-trans-selective cyclization can be accomplished simply by changing the additives from NiI2 to HMPA during reductive cyclization conducted in H2O–THF. Total synthesis of (−)-kainic acid and (+)-allo-kainic acid, which are pyrrolidine alkaloids used in neuroscience and neuropharmacology as useful molecular probes, was successfully achieved by using the stereo-complementary ring closure reactions promoted by SmI2 for the construction of the 2,3,4-trisubsituted pyrrolidine scaffold of kainoids.

Graphical abstract: Total synthesis of (−)-kainic acid and (+)-allo-kainic acid through SmI2-mediated intramolecular coupling between allyl chloride and an α,β-unsaturated ester

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Publication details

The article was received on 13 Jun 2017, accepted on 11 Jul 2017 and first published on 11 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01427A
Citation: Org. Biomol. Chem., 2017,15, 6557-6566
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    Total synthesis of (−)-kainic acid and (+)-allo-kainic acid through SmI2-mediated intramolecular coupling between allyl chloride and an α,β-unsaturated ester

    J. Suzuki, N. Miyano, S. Yashiro, T. Umezawa and F. Matsuda, Org. Biomol. Chem., 2017, 15, 6557
    DOI: 10.1039/C7OB01427A

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