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Synthetic Studies on Viridin Skeleton through Regio- and Stereoselective Functionalization of the AE-Ring Moiety
Synlett ( IF 2 ) Pub Date : 2021-06-11 , DOI: 10.1055/a-1527-3781
Shuji Akai 1 , Shuhei Hori 1 , Sho Ishida 2 , Go Itoh 2 , Koji Sugiyama 1 , Chiharu Yuki 1 , Masahiro Egi 3 , Kenzo Yahata 1 , Takashi Ikawa 1
Affiliation  

4,5,6,7-Tetrahydroisobenzofurans, corresponding to the AC(D)E ring structure of viridin and equipped with required substituents on the A-ring, were synthesized via the Diels-Alder adduct of a furan derivative and maleic anhydride with high regio- and stereoselectivities. The key steps of this work include the regioselective opening of the tetrahydrofuran, stereoselective epoxidation, and AlMe3-mediated regioselective epoxide opening followed by stereoselective C-methylation.

中文翻译:

通过 AE 环部分的区域和立体选择性功能化对 Viridin 骨架的合成研究

通过呋喃衍生物和马来酸酐的狄尔斯-阿尔德加合物合成了 4,5,6,7-四氢异苯并呋喃,对应于绿色素的 AC(D)E 环结构并在 A 环上配备了所需的取代基。区域选择性和立体选择性。这项工作的关键步骤包括四氢呋喃的区域选择性开放、立体选择性环氧化和 AlMe3 介导的区域选择性环氧化物开放,然后是立体选择性 C-甲基化。
更新日期:2021-06-30
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