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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Bibliographic Details
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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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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2024.134064