Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid

Goswami, Rajesh; Moloney, Mark G.

doi:10.1039/a906297a

Cited by 23 publications

(12 citation statements)

References 39 publications

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“…50 The stereocontrol in reactions of lactam templates has been of some interest 32,43,51-53 and we have shown that unusual stereocontrol is possible for bicyclic lactam 1b by the application of remote steric effects around the ring periphery. 54 We have demonstrated that this approach provides access to novel kainoid analogues 22, 24 and conformationally well-defined amino acid analogues, 55 and report here its application to the synthesis of analogues of penmacric acid.…”

Section: Introductionmentioning

confidence: 97%

Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues

et al. 2003

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Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.

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Section: Introductionmentioning

confidence: 97%

Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues

et al. 2003

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“…Reduction of nitriles 3a, 4a and 4b (NaBH 4 , CoCl 2 •H 2 O or NaBH 4 , NiCl 2 •H 2 O) 29 followed by in situ cyclisation of the Fig. 2 X-ray structures for 3a and 4b (ellipsoids at 50% probability level).…”

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confidence: 99%

Spirocyclic systems derived from pyroglutamic acid

et al. 2011

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“…Some of this work has been published in a preliminary form. 54 Fig. 1 We first examined the alkylation of lactam 1a with bromoacetonitrile; this would generate a conformationally restricted lysine derivative (Scheme 1).…”

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Stereoselective synthesis of conformationally constrained ω-amino acid analogues from pyroglutamic acid

et al. 2005

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Bicyclic lactams derived from pyroglutamic acid provide a useful scaffold for synthesis of conformationally restricted analogues of lysine, ornithine and glutamine, as well as an Ala-Ala dipeptide analogue. Amino alcohol and carboxylic acid derivatives are accessible from a common intermediate. In this strategy, the bicyclic lactam system not only controls, but also facilitates the determination of the stereochemistry of the synthetic intermediates.

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Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid

Cited by 23 publications

References 39 publications

Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues

Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues

Spirocyclic systems derived from pyroglutamic acid

Stereoselective synthesis of conformationally constrained ω-amino acid analogues from pyroglutamic acid

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