Premium
Total Synthesis of Kopsinitarine E
Author(s) -
Nagaraju Karre,
Ni Dongshun,
Ma Dawei
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011093
Subject(s) - hemiaminal , chemistry , total synthesis , intramolecular force , amide , stereochemistry , pinacol , phenanthridine , combinatorial chemistry , organic chemistry , catalysis
Kopsinitarines A–E are complex octacyclic caged Kopsia alkaloids 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 SmI 2 ‐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.