Enantioselective Total Synthesis of (+)-Stephadiamine through Bioinspired Aza-Benzilic Acid Type Rearrangement
| Autor: | Minami Odagi, Taisei Matoba, Kazuo Nagasawa, Keisuke Hosoya |
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| Rok vydání: | 2021 |
| Předmět: |
Aza Compounds
Stereochemistry Chemistry Benzilic acid Enantioselective synthesis Total synthesis Regioselectivity Stereoisomerism General Chemistry 010402 general chemistry Heterocyclic Compounds 4 or More Rings 01 natural sciences Biochemistry Catalysis Coupling reaction 0104 chemical sciences Stereocenter chemistry.chemical_compound Alkaloids Colloid and Surface Chemistry Metals Hasubanan Rearrangement reaction |
| Zdroj: | Journal of the American Chemical Society. 143:2699-2704 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.1c00047 |
| Popis: | We report the first enantioselective total syntheses of the hasubanan alkaloid (-)-metaphanine and the norhasubanan alkaloid (+)-stephadiamine. Key features of these syntheses include diastereoselective oxidative phenolic coupling reaction and subsequent regioselective intramolecular aza-Michael reaction, which efficiently construct the hasubanan skeleton with the all-carbon quaternary stereogenic center at C13. Based on our hypothesis regarding the biosynthetic pathway of (+)-stephadiamine, we found that (-)-metaphanine is easily converted to (+)-stephadiamine via aza-benzilic acid type rearrangement reaction. |
| Databáze: | OpenAIRE |
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