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 inTetrahedron Vol. 161
Main Authors He, Yi-Fan, Meng, Fan-cui, Cai, Tian-Tian, Yin-Liu, Xie, Yun-Dong, Zhou, Jing, Yan, Hao, Liu, Ji-Ping, Han, Chao-Jun, Shi, Yong-Heng
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.07.2024
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Abstract 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. [Display omitted]
AbstractList 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. [Display omitted]
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 BF 3 & sdot;Et 2 O and H 2 O. 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.
ArticleNumber 134064
Author Cai, Tian-Tian
Yin-Liu
Zhou, Jing
Xie, Yun-Dong
He, Yi-Fan
Han, Chao-Jun
Yan, Hao
Liu, Ji-Ping
Shi, Yong-Heng
Meng, Fan-cui
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Snippet The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S-isomers; however, the challenge lies in the selective synthesis of...
The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S -isomers; however, the challenge lies in the selective synthesis of...
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elsevier
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Publisher
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title A minimalist approach to the stereoselective synthesis of 1R-alkoxygenipins
URI https://dx.doi.org/10.1016/j.tet.2024.134064
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