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

[21] A concise total synthesis of bruceolline E
Jordan, Jason A.
Gribble, Gordon W.
Badenock, Jeanese C.
TETRAHEDRON LETTERS, 2011, 52 (50) : 6772 - 6774
[22] Enantiospecific Total Synthesis of (-)-Bengamide E
Metri, Prashant K.
Schiess, Raphael
Prasad, Kavirayani R.
CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (02) : 488 - 493
[23] Total Synthesis of Pallamolides A-E
Zhang, Yu
Chen, Lijun
Jia, Yanxing
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (20)
[24] Stereoselective Total Synthesis of (±)-Alstoscholarisine E
Wood, Michael D.
Klosowski, Daniel W.
Martin, Stephen F.
ORGANIC LETTERS, 2020, 22 (03) : 786 - 790
[25] Biomimetic Total Synthesis of (+)-Gelsemine
Zhou, Xuan
Xiao, Tao
Iwama, Yusuke
Qin, Yong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) : 4909 - 4912
[26] Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine A
Nash, Aaron
Qi, Xiangbing
Maity, Pradip
Owens, Kyle
Tambar, Uttam K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (23) : 6888 - 6891
[27] Concise Total Synthesis of Tronocarpine
Nakayama, Atsushi
Nakamura, Tenta
Zaima, Toshihiro
Fujimoto, Saho
Karanjit, Sangita
Namba, Kosuke
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (02) : 635 - 639
[28] Enantioselective Total Synthesis of (-)-Deoxoapodine
Kang, Taek
White, Kolby L.
Mann, Tyler J.
Hoveyda, Amir H.
Movassaghi, Mohammad
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (44) : 13857 - 13860
[29] Stereoselective Total Synthesis of Paecilomycins E and F
Bhunia, Nisith
Das, Biswanath
SYNTHESIS-STUTTGART, 2015, 47 (10): : 1499 - 1509
[30] Asymmetric Total Synthesis of Aglacins A, B, and E
Xu, Mengmeng
Hou, Min
He, Haibing
Gao, Shuanhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (30) : 16655 - 16660

← 1 2 3 4 5 →