Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines

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Abstract

Open-chain N-Cbz-protected-peptidoyl benzotriazolides are converted by a novel lactamization strategy using proline as a turn introducer into both symmetrical (5a-c and 11a-c) and unsymmetrical (19a-e) bis-2,5-diketopiperazines (bis-2,5-DKPs), previously recognized as difficult targets. © 2013 American Chemical Society.

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Ha, K., Lebedyeva, I., Li, Z., Martin, K., Williams, B., Faby, E., … Katritzky, A. R. (2013). Conformationally assisted lactamizations for the synthesis of symmetrical and unsymmetrical bis-2,5-diketopiperazines. Journal of Organic Chemistry, 78(17), 8510–8523. https://doi.org/10.1021/jo401235k

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