Journal
SCIENCE CHINA-CHEMISTRY
Volume 63, Issue 8, Pages 1091-1099Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-020-9754-7
Keywords
bifunctional phosphonium salts; benzofused tropanes; cyclic azomethine ylides; cyclodearomatization; antitumor activity
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Funding
- National Natural Science Foundation of China [21971165, 21921002, 81630101]
- National Key Research and Development Program of China [2018YFA0903500]
- 1000-Youth Talents Program [YJ201702]
- Fundamental Research Funds for the Central Universities
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Structurally fused heterocycles encompassing a centerpiece of benzotropane are significant scaffolds with a plethora of promising biological activities, but such molecular architectures pose a long-standing daunting synthetic challenge. Herein, we reported a highly efficient asymmetric cyclodearomatization of 2-nitrobenzofurans with cyclic azomethine ylides by employing bifunctional phosphonium salts as phase-transfer catalysts. Under optimized reaction conditions, a diverse array of polycyclic benzofused tropane derivatives with four contiguous 4 degrees/3 degrees stereocenters were readily synthesized in both high yields and diastereoselectivities with up to >99% ee. The practicality and utility of this protocol were further demonstrated by the scaled-up reaction and facile elaborations. Moreover, preliminary investigations into their antitumor activities were also presented.
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