| アイテムタイプ |
文献 / Documents(1) |
| 公開日 |
2021-09-07 |
| アクセス権 |
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アクセス権 |
open access |
| 資源タイプ |
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資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
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資源タイプ |
journal article |
| 出版社版DOI |
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関連識別子 |
https://doi.org/10.1039/D1SC03260G |
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関連名称 |
10.1039/D1SC03260G |
| 出版タイプ |
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出版タイプ |
VoR |
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出版タイプResource |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| タイトル |
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タイトル |
Efficient construction of the hexacyclic ring core of palau'amine : the pKa concept for proceeding with unfavorable equilibrium reactions |
| 著者 |
オオハシ, エイサク
カランジット, サンギータ
中山, 淳
タケウチ, コウヘイ
Emam, Sherif E.
安藤, 英紀
石田, 竜弘
難波, 康祐
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| 抄録 |
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内容記述 |
Palau'amine has received a great deal of attention as an attractive synthetic target due to its intriguing molecular architecture and significant immunosuppressive activity, and we achieved its total synthesis in 2015. However, the synthesized palau'amine has not been readily applicable to the mechanistic study of immunosuppressive activity, because it requires 45 longest linear steps from a commercially available compound. Here, we report the short-step construction of the ABCDEF hexacyclic ring core of palau'amine. The construction of the CDE tricyclic ring core in a single step is achieved by our pKa concept for proceeding with unfavorable equilibrium reactions, and a palau'amine analog without the aminomethyl and chloride groups is synthesized in 20 longest linear steps from the same starting material. The palau'amine analog is confirmed to retain the immunosuppressive activity. The present synthetic approach for a palau'amine analog has the potential for use in the development of palau'amine probes for mechanistic elucidation. |
| 書誌情報 |
en : Chemical Science
巻 12,
号 36,
p. 12201-12210,
発行日 2021-08-11
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| 収録物ID |
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収録物識別子タイプ |
ISSN |
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収録物識別子 |
20416539 |
| 出版者 |
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出版者 |
The Royal Society of Chemistry |
| 権利情報 |
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権利情報 |
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence(https://creativecommons.org/licenses/by/3.0/). |
| EID |
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識別子 |
381696 |
| 言語 |
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言語 |
eng |
cs_12_36_12201.pdf (1.77 MB)
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