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Issue 19, 2000
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The stereoselective preparation of substituted pyrrolidines using titanium- and zirconium-mediated diene metallabicyclisation methodology: the total synthesis of (−)-α-kainic acid

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Abstract

Zirconium- and titanium-mediated diene metallabicyclisation–elimination–functionalisation have been compared, contrasted and utilised for the preparation of 3,4-disubstituted and 2,3,4-trisubstituted pyrrolidines in high yield and excellent stereoselectivity. The zirconium-mediated methodology has been employed as the key step in a partial synthesis of (−)-α-kainic acid starting from D-serine, but the key metallabicyclisation sequence proceeded with poor stereocontrol. By contrast, the total synthesis of (−)-α-kainic acid starting from L-serine was accomplished using a titanium-mediated cyclisation sequence which proceeded with excellent stereocontrol. Novel kainoids and piperidines are also reported.

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Article information


Submitted
20 Jul 2000
Accepted
08 Aug 2000
First published
18 Sep 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3194-3204
Article type
Paper

The stereoselective preparation of substituted pyrrolidines using titanium- and zirconium-mediated diene metallabicyclisation methodology: the total synthesis of (−)-α-kainic acid

A. D. Campbell, T. M. Raynham and R. J. K. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3194
DOI: 10.1039/B005853J

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