Efficient construction of the hexacyclic ring core of palau'amine : the pKa concept for proceeding with unfavorable equilibrium reactions
説明
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.
収録刊行物
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- Chemical Science
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Chemical Science 12 (36), 12201-12210, 2021-08-11
The Royal Society of Chemistry
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詳細情報 詳細情報について
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- CRID
- 1050007902966013312
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- NII論文ID
- 120007146083
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- ISSN
- 20416539
- 20416520
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- 本文言語コード
- en
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- 資料種別
- journal article
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- データソース種別
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