Borylation via iridium catalysed C-H activation: a new concise route to duocarmycin derivatives

被引：0

作者：

Cominetti, Marco M. D. ^{[1
]}

Goddard, Zoe R. ^{[1
]}

Hood, Bethany R. ^{[1
]}

Beekman, Andrew M. ^{[1
]}

O'Connell, Maria A. ^{[1
]}

Searcey, Mark ^{[1
]}

机构：

[1] Univ East Anglia, Sch Pharm, Norwich Res Pk, Norwich NR4 7TJ, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 27期

基金：

英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;

关键词：

2-SUBSTITUTED INDOLES; CYTOSTATIC CC-1065; BORONIC ACIDS; PRODRUGS; ANALOGS; SUBJECT; DESIGN;

D O I：

10.1039/d4ob00814f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the ethyl ester analogue of the ultrapotent antitumour antibiotic seco-duocarmycin SA has been achieved in eleven linear steps from commercially available starting materials. The DSA alkylation subunit can be made in ten linear steps from the same precursor. The route involves C-H activation at the equivalent of the C7 position on indole leading to a borylated intermediate 9 that is stable enough for peptide coupling reactions but can be easily converted to the free hydroxyl analogue.

引用

页码：5603 / 5607

页数：5

共 50 条

[21] Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C-H bond activation
Cheng, Chien
Shih, Yu-Chiao
Chen, Hui-Ting
Chien, Tun-Cheng
TETRAHEDRON, 2013, 69 (04) : 1387 - 1396
[22] Tridentate κ3-P,P,C iridium complexes: influence of ligand saturation on intramolecular C-H bond activation
Demchuk, Mitchell J.
Zurakowski, Joseph A.
Drover, Marcus W.
CHEMICAL COMMUNICATIONS, 2024, 60 (59) : 7566 - 7569
[23] Consequent Construction of C-C and C-N Bonds via Palladium-Catalyzed Dual C-H Activation: Synthesis of Benzo[c]cinnoline Derivatives
Li, Hongsheng
Zhao, Junhao
Yi, Songjian
Hu, Kongzhen
Feng, Pengju
ORGANOMETALLICS, 2021, 40 (07) : 880 - 889
[24] Direct arylation of cyclic enamides via Pd(II)-catalyzed C-H activation
Zhou, Hai
Chung, Wan-Jun
Xu, Yun-He
Loh, Teck-Peng
CHEMICAL COMMUNICATIONS, 2009, (23) : 3472 - 3474
[25] Pd-catalyzed oxidative coupling with organometallic reagents via C-H activation
Sun, Chang-Liang
Li, Bi-Jie
Shi, Zhang-Jie
CHEMICAL COMMUNICATIONS, 2010, 46 (05) : 677 - 685
[26] Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation
Yu, Yi-Yun
Georg, Gunda I.
CHEMICAL COMMUNICATIONS, 2013, 49 (35) : 3694 - 3696
[27] Ferroceneboronic Acid and Derivatives: Synthesis, Structure, Electronic Properties, and Reactivity in Directed C-H Bond Activation
Erb, William
Hurvois, Jean-Pierre
Roisnel, Thierry
Dorcet, Vincent
ORGANOMETALLICS, 2018, 37 (21) : 3780 - 3790
[28] Catalytic Borylation of SCF3-Functionalized Arenes by Rhodium(I) Boryl Complexes: Regioselective C-H Activation at the ortho-Position
Kallaene, Sabrina I.
Braun, Thomas
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (35) : 9311 - 9315
[29] Cross-Dehydrogenative Coupling Polymerization via C-H Activation for the Synthesis of Conjugated Polymers
Chakraborty, Baitan
Luscombe, Christine K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (21)
[30] Regioselective hydroarylation and arylation of maleimides with indazoles via a Rh(iii)-catalyzed C-H activation
Ghosh, Asim Kumar
Samanta, Sadhanendu
Ghosh, Payel
Neogi, Sukanya
Hajra, Alakananda
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (16) : 3093 - 3097

← 1 2 3 4 5 →