Unified Total Synthesis of Tryptophan-based Dimeric Diketopiperazine Alkaloids

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  • Ishikawa Hayato
    Department of Chemistry, Graduate School of Science and Technology, Kumamoto University

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  • トリプトファン由来二量体型ジケトピペラジンアルカロイド類の網羅的全合成
  • トリプトファン ユライ ニリョウ タイケイ ジケトピペラジンアルカロイドルイ ノ モウラテキ ゼン ゴウセイ

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Abstract

A concise synthesis of WIN 64821 (1), eurocristatine (2), 15,15’-bis-epi-eurocristatine (3), ditryptophenaline (4), ditryptoleucine A (6), WIN 64745 (7), cristatumin C (8), asperdimin (9), naseseazine A (10), and naseseazine B (11) is detailed based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and one-pot procedure for construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10% up to 27%. In addition, 1’-(2-phenylethylene)-ditryptophenaline (5) was synthesized using three one-pot operations. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin-specific protease 7 (USP7) and foam cell formation in macrophages.

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