Unified Total Synthesis of Tryptophan-based Dimeric Diketopiperazine Alkaloids
-
- Ishikawa Hayato
- Department of Chemistry, Graduate School of Science and Technology, Kumamoto University
Bibliographic Information
- Other Title
-
- 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
Search this article
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.
Journal
-
- Journal of Synthetic Organic Chemistry, Japan
-
Journal of Synthetic Organic Chemistry, Japan 74 (2), 104-116, 2016
The Society of Synthetic Organic Chemistry, Japan
- Tweet
Keywords
Details 詳細情報について
-
- CRID
- 1390001205340579712
-
- NII Article ID
- 130005138524
-
- NII Book ID
- AN0024521X
-
- ISSN
- 18836526
- 00379980
-
- NDL BIB ID
- 027099887
-
- Text Lang
- ja
-
- Data Source
-
- JaLC
- NDL
- Crossref
- CiNii Articles
-
- Abstract License Flag
- Disallowed