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

共 50 条

[1] Total Synthesis of (±)-Strictamine
Ren, Weiwu
Wang, Qian
Zhu, Jieping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (10) : 3500 - 3503
[2] Total synthesis of cyclopiamide A and speradine E
Nakhla, Mina C.
Weeks, Kendall N.
Villalobos, Mauricio Navarro
Wood, John L.
TETRAHEDRON, 2018, 74 (38) : 5085 - 5088
[3] Total Synthesis of (+)-Daphmanidin E
Weiss, Matthias E.
Carreira, Erick M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11501 - 11505
[4] Total Synthesis of (+)-Haplophytine
Ueda, Hirofumi
Satoh, Hitoshi
Matsumoto, Koji
Sugimoto, Kenji
Fukuyama, Tohru
Tokuyama, Hidetoshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (41) : 7600 - 7603
[5] Total Synthesis of (±)-Aspidophylline A
Ren, Weiwu
Wang, Qian
Zhu, Jieping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) : 1818 - 1821
[6] A Total Synthesis of Salinosporamide A
Marx, Leo B.
Burton, Jonathan W.
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (26) : 6747 - +
[7] Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E
Myeong, In-Soo
Avci, Nadide Hazal
Movassaghi, Mohammad
ORGANIC LETTERS, 2021, 23 (23) : 9118 - 9122
[8] Total Synthesis of Dictyodendrins A-E
Tokuyama, Hidetoshi
Okano, Kentaro
Fujiwara, Hideto
Noji, Toshiharu
Fukuyama, Tohru
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) : 560 - 572
[9] Total Synthesis and Biological Evaluation of Jerantinine E
Frei, Reto
Staedler, Davide
Raja, Aruna
Franke, Raimo
Sasse, Florenz
Gerber-Lemaire, Sandrine
Waser, Jerome
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13373 - 13376
[10] An overview: total synthesis of arborisidine, and arbornamine
Yadav, Gitanjali
Megha, Sangeeta
Yadav, Sangeeta
Tomar, Ravi
MOLECULAR DIVERSITY, 2024, : 2783 - 2797

← 1 2 3 4 5 →