Freie Universität Berlin, Institute of Chemistry and Biochemistry, Takustrasse 3, 14195, Berlin, Germany.
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.
Angew Chem Int Ed Engl. 2021 Jun 7;60(24):13591-13596. doi: 10.1002/anie.202102518. Epub 2021 May 1.
A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.
发展了一种用于多环生物碱合成的互补双羰基激活策略。成功的应用包括四环生物碱哈尔拉林和哈尔马林的合成、五环吲哚喹啉生物碱诺替托比林和八环β-咔啉生物碱佩甘胺 A 的合成。后一种合成具有无保护基组装和不对称二磺酰亚胺催化的环化反应。此外，还实现了毛叶番荔枝碱、去甲布瑞宁、10-去溴阿尔布瑞辛 A 以及吲哚生物碱钩藤碱和异钩藤碱的形式合成。最后，完成了小檗碱生物碱藜芦定 B 的简洁合成。
