Total Synthesis of Kopsinitarine E

被引：21

作者：

Nagaraju, Karre ^{[1
]}

Ni, Dongshun ^{[1
]}

Ma, Dawei ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem,Ctr Excell, 345 Lingling Lu, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 49期

基金：

中国国家自然科学基金;

关键词：

cyclization; indole alkaloids; Mannich reaction; semi-pinacol rearrangement; total synthesis; CATALYZED DECARBOXYLATIVE ALLYLATION; CARBOXYLIC-ACID DERIVATIVES; CONCISE TOTAL-SYNTHESIS; INDOLE ALKALOIDS; SEMIPINACOL REARRANGEMENT; CHEMOSELECTIVE REDUCTION; NATURAL-PRODUCTS; MANNICH REACTION; TERTIARY AMIDES; KOPSIA-TENUIS;

D O I：

10.1002/anie.202011093

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：22039 / 22042

页数：4

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