A minimalist approach to the stereoselective synthesis of 1R-alkoxygenipins
The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S-isomers; however, the challenge lies in the selective synthesis of these compounds. A streamlined and highly effective approach to achieve stereoselective 1R-alkyloxygenipins involved the use of a carefully bal...
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Published in | Tetrahedron Vol. 161 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
17.07.2024
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S-isomers; however, the challenge lies in the selective synthesis of these compounds. A streamlined and highly effective approach to achieve stereoselective 1R-alkyloxygenipins involved the use of a carefully balanced mixture of Lewis acid catalytic reagents, specifically BF3·Et2O and H2O. This method emerged as the optimal choice after evaluating various synthetic routes, encompassing 1-OH and 10-OH substitutions, different Lewis acids, and their respective ratios as catalysts. The possible mechansim of the catalyst for genipin was investigated. Particularly, the method with non-strict conditions for the synthesis of 1R-alkoxygenipins was underscored by its operational simplicity, stability, and low energy consumption. This approach not only streamlined the synthetic process but also established a robust foundation for future bioactivity studies on 1R-alkyloxygenipins.
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2024.134064 |