Studies towards the total synthesis of (-)-α-Kainic acid

Lai, Jason (2012) Studies towards the total synthesis of (-)-α-Kainic acid. Doctoral thesis (PhD), University of Sussex.

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Abstract

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trans-4-Hydroxy-L-proline (2.2) was converted to a key oxazolidinone precursor (2.1) by an improved Greenwood’s procedure.47,48 The diastereofacial selective property of (2.1) led to a stereo-controlled 1,3-dipolar cycloaddition and gave a single tricyclic diastereomer (2.20). The N-O bond of the resulting isoxazoline (2.20) was cleaved by a reductive ring-opening, followed by an elimination to give enone (2.26). The enone (2.26) was converted to a -silanol (2.33) by a nucleophillic addition with LiCH2Si(CH3)3 and then an acetylation to (2.27) was attempted.
Addition of Gilman reagent to the enone (2.26) resulting a diastereoselective 1,4-nucleophillic addition and afforded the C-2,C-3 trans, C-3,C-4 cis sterically favoued bicyclic pyrrolidine (2.38) as the only diastereomer. All that remains for the synthesis of kainic acid (1.1) are olefination, ring-opening of carbamate, oxidation and deprotection.

Item Type: Thesis (Doctoral)
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: Library Cataloguing
Date Deposited: 28 Aug 2012 05:44
Last Modified: 04 Sep 2015 14:20
URI: http://sro.sussex.ac.uk/id/eprint/40314

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