Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 49, Pages 22039-22042Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202011093
Keywords
cyclization; indole alkaloids; Mannich reaction; semi-pinacol rearrangement; total synthesis
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Funding
- Chinese Academy of Sciences
- Strategic Priority Research Program [XDB20020200, QYZDJ-SSW-SLH029]
- National Natural Science Foundation of China [21621002, 21831009]
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Kopsinitarines A-E are complex octacyclic cagedKopsiaalkaloids with strained cage skeletons and a unique cyclic hemiaminal bridge that makes total synthesis challenging. Herein, we disclose the first total synthesis of kopsinitarine E. The key synthetic features include a SmI2-mediated radical cascade cyclization and a subsequent semi-pinacol rearrangement to install the key carbocyclic skeleton, a chemoselective hydrosilyl amide reduction to construct the hemiaminal ether bridge, and an intramolecular Mannich reaction to establish the highly strained cage system.
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